How to Meet Guys in Person: Six Tips From a Man


By Julian Makar

Swipe left, swipe right. I’ve heard from many female friends that they are getting tired of using social dating apps. They want to know how to meet guys in person, to have a conversation, drinks, and flirt.

Dating online is convenient but exhausting, and doesn’t create the same excitement as meeting someone in person. It can be difficult to choose from hundreds of dating profiles that all start to look the same. And often there is a sense of pressure and awkwardness when you meet for the first time, rather than flirtatiousness and chemistry. For many people, this is a difficult foundation from which to build a relationship.

Thankfully, there are still opportunities to meet guys in person. The best way to meet men this way is to choose your time and place carefully and make sure you’re fully prepared for the occasion.

Let me provide you with six tips that will help you maximize your opportunity to meet guys in person:

1.  Timing is Everything

If you’re going out with the goal of meeting men, you need to plan your timing. I recommend trying to meet men on Thursday evenings after work. Thursday tends to be the most popular day for happy hour specials and industry events, both of which draw single people out to socialize.

By Thursday evening, most people are beginning to get excited in anticipation of the weekend, so they’ll let loose a little more than on an earlier night of the week. However, unlike Friday and Saturday nights, most men you’ll meet probably aren’t getting blackout drunk with the aim of getting laid. Instead, they’re meeting up with friends for a low-key evening of drinks, conversation, and fun. The opportunity is ripe for an encounter that can lead to something better than a drunken midnight makeout at the club.

Thursday happy hour tends to draw a larger proportion of mature men, aged 30-40, who are well established in their careers and lifestyles. At this stage, most men aren’t spending their Saturday nights trying to meet women on the dance floor at the club. If this is how you are accustomed to meeting guys, you’ll need to break out of your comfort zone a bit and try something different. Otherwise, you’ll continue to meet men in their twenties who may or may not be looking for something more than a hookup. Which brings me to my next point:

2.  Location, Location, Location

Now that you know the best evening to meet men, you should plan where you’ll go to meet them. There are tons of options in Toronto (and any city), but to help you narrow it down, I’ll emphasize three points:

  • Think about price point – this will determine the type of man you’ll find there. Avoid cheapie bars that attract students and people under the age of 25. Choose somewhere that the price point is a bit higher if you can afford it. Part of the benefit of going out for Thursday happy hour is that most places will have drink specials that make it more affordable.
  • Neighbourhood matters – you’ll find different types of men in different neighbourhoods. If you want to meet wealthy men who work in law or finance, choose a trendy spot in the financial district. If you want to meet guys who are into sports, choose a pub near a sports venue (for example, a bar near the ACC or Rogers Centre on game night.) If you want to meet a hipster or artist type, travel out to Ossington or Dundas West. Whatever your taste, opt for a classy variant of your intended destination, keeping my previous point in mind.
  • Do your research – talk with other girlfriends and guy friends to learn where they’ve had luck meeting guys before, and where they’d recommend going. Look online and read reviews for different places in your city. Keep track of your experiences at the places you’ve tried, and go back to the ones that seemed promising.

Location also matters once you arrive at your destination. Always locate yourself strategically. I recommend standing or sitting at the bar, as this is the place you’re most likely to interact with multiple people. Men will come up to get drinks, you’ll be able to chat with the bartender, and the other people sitting at the bar will likely be open to chatting.

You’ll also have a great vantage point from which to see and be seen, which is key. If we can’t see you, we definitely won’t approach you. Aim to be noticeable, which means being visible, centrally located, and sociable. Being part of the action is what makes sitting at the bar fun. Plus, if the bartender is cute, you can flirt with him and maybe some free drinks will come your way.

3.  Don’t Go With a Group

There is nothing more intimidating than a big group of six girls chatting and laughing amongst themselves. While guys may want to approach you in this context, only the brashest (or drunkest) among us will actually do it. Then the challenge is, how can we tactfully focus in on the one we’re interested in without offending the others? It’s too delicate a situation for most guys to attempt.

Instead, bring two girlfriends at the most. This is critical to the operation. The best number is two, but three can work, and so can flying solo if you’re comfortable chatting up strangers or reading a book at the bar. However going with one girlfriend is easiest because you have someone to chat and have fun with, even if you don’t end up finding a guy there.

4.  Unplug and Stay That Way

Put down the phone. Better yet, leave it in your bag on silent.

I know this can be difficult to do, but how do you expect us to notice you when you’re hunched over with your eyes glued to a screen? How will you make eye contact with that cute guy 15 feet away when you’re busy scrolling through Instagram? It’s a turnoff, and it takes your eyes off the prize.

Even if you’re a bit socially anxious or want something to entertain you while your girlfriend goes to the washroom, don’t! The moments that you’re alone are the moments you’re most likely to be approached – if you look approachable (which you don’t, when you’re focused on your phone.)

Just enjoy being in the space, and let yourself experience it – even if it feels a bit weird. Look around at the room, chat with the bartender, and sip your drink. This will set you apart from everyone else whose noses are buried in their phones.

5.  Smile, Laugh, and Look Happy

Women often assume that men will approach the prettiest girl in the room. However what we are actually most attracted to are the women who make themselves stand out by smiling, laughing, and looking like they love life. These women are magnetic, and we want to approach them.

When you arrive at the bar, make sure you project this. Walk confidently with your chin up and shoulders back. Sit tall in your seat and act alert and engaged – scan the room, smile, and chat with the people around you. Orient your body so that you seem open and approachable. This evening is not for serious conversations about politics and religion – it’s for you to go out and have fun!

6.  Dress the Part

Much as men don’t approach women solely for their looks, I won’t lie and tell you that appearance doesn’t matter to us – it does. Quite a lot. We are visual, and the first impression a woman makes influences our perception of her for the entire relationship.

We are more inclined to find you attractive if you look like you’ve put effort into your grooming, outfit, and appearance. We probably won’t notice your freshly done manicure or intricately winged eyeliner. But we will notice if your hair is clean, your outfit looks sexy, and your shoes have a heel.

When going out, aim for sexy, not for cute. Cute can work to your advantage on a date or in a relationship, but it probably won’t help you get approached. Dress in clothing that is trendy and flattering, like you would wear on a first date. You can’t go wrong with a form-fitting dress or office chic look. Steer clear of athleisure wear, sweatpants, and baggy clothes – these won’t help you stand out.

Know that we will notice your shoes. Don’t wear beat-up sneakers or clunky boots. Heels of any sort are the most attractive and can make all the difference between looking cute and looking gorgeous.

Wear at least a bit of makeup (even if you go for the “au natural” look, which can be very attractive.) Keep your hair down if you can. I won’t tell you how to style your hair because we have different tastes – some guys love shiny smooth hair, others love a sexy curly or wavy look. Just style it in a way that makes you feel sexy and confident.

Taking all these tips into account, your aura of confidence, happiness, and openness will make you stand out from everyone else in a crowded room. Guys will be certain to notice you, and won’t be able to resist approaching you to say hello.

Written by Julian Makar
Edited by Nicole Gaasenbeek


Why Do I Want What I Can’t Have? How to Stop Chasing the Wrong Guys

Why Do I Want What I Can't Have

Wanting what we can’t have is one of the oldest – and most painful – mysteries of the human condition. When it comes to dating, this pain falls on one of two ends of the scale: either you’re completely in love with a guy who is unattainable and treats you like crap, or you’re apathetic to the men who cross your path, and can’t find the smallest spark that seems worth pursuing.

Either situation feels absolutely devastating. And often they’re related – you’ll escape the misery of unrequited love or a destructive relationship, only to find that nobody else you meet seems worthwhile. I’ve been through it, and remember clearly the frustration and despair that can take over for weeks or months.

My first long-ish term boyfriend (who I met at the age of 22) was brilliant, hilariously witty, and extremely attractive in a “charming scoundrel” sort of way. He pursued me passionately but haphazardly, going from 0 to 100 in two seconds flat when we were together, then 100 to 0 as soon as we’d parted ways.

Sometimes I wouldn’t hear from him for days or weeks at a time. He’d often cancel on me at the last minute because he “had to do his laundry” or “took a nap and forgot to set an alarm.” One New Year’s Eve passed without so much as a text from him.

Instead of thinking “What am I doing wasting time on this guy who clearly sucks and doesn’t care much for me?” I thought, “Oh god, what am I doing wrong? How can I fix it? What can I do to make him love me more? I can’t lose him!”

When the relationship inevitably ended – with a phonecall from him, after weeks of evasiveness – I was sure I would never feel the same way about anyone, ever again. And for a few months afterwards, that really did seem to be the case.

Even once I got through the initial shock and devastation of getting dumped, I wasn’t prepared for what the dating world had in store for me. I remember kicking my butt off the couch and getting back out there as soon as I thought I was ready, only to find I had zero interest in any of the guys I was meeting.

Sure, I met some seemingly good guys, had some interesting conversations, and experienced some fun adventures. But the chemistry that I was waiting for just never seemed to be there – so I never accepted a second date.

After a few weeks of this, there were more and more days that I couldn’t peel myself off the couch to fetch a bag of chips, let alone get dressed up and go out on another date. On the worst days, I found myself wondering, “Is it me? Am I doing something wrong? Or is it them? Does every guy suck? Is it all just hopeless?”

Of course, there was nothing wrong with me, and every guy certainly does not suck. The truth was, I needed to spend more time understanding the expectations and habits that were guiding my dating choices. After all, they were the same expectations and habits that had landed me in such a terrible position in the first place.

I started questioning why I was only attracted to guys who didn’t have the same level of interest in me. I was rarely interested in any guy I met until I’d had some time to get to know him. I had a history of “friend-zoning” guys who I later developed intense attraction to, but only after they had firmly friend-zoned me.

This led me to wonder just how many guys I was rejecting after the first date for “lack of chemistry” when the potential for chemistry was actually there, waiting to be uncovered if I could slow down and move at a different pace. I wrote an entire article specifically about chemistry, explaining how you can test whether the potential for chemistry is there – even when it isn’t obvious right away.

Many of my girlfriends had struggled with similar experiences and patterns, so I knew I wasn’t the only one facing this issue. After a great deal of reading, research, and active dating, I realized the crucial mistake I was making:

I was still seeking crushes, not relationships.

Why We Chase the Wrong Guys

The fact of the matter is this: the world is filled with amazing men. Just think about the great men who are in your life already. Men like your dad, brothers, cousins, or guy friends. Men you love and trust, who treat women with respect and kindness.

But for some reason, we often end up dating the not-so-good guys instead – those who take, but never give. The guys who have charisma, confidence, and good looks, but will just as soon ignore you as booty call you.

Some men are here today and gone tomorrow, back again only when they want something from you. And more often than not, we’re ready and waiting – to give, and give, and give, hoping that once we’ve given enough, we’ll have earned their love.

These are the guys we fall for in high school and university. At that age, attraction is so dazzling that we barely notice pesky details like the way a guy treats us. We don’t ask questions, or exercise much judgment, because we’re caught up in the mad rush of hormones and the excruciating ups and downs of a crush.

As a teenager, you might have crushed on the same guy for months or even years without reciprocation. You experienced dizzying highs when he’d chat you up at a party, and crashing lows when he ignored you the next day in the halls. It was a wild cycle of excitement and disappointment, reward and punishment.

These emotions are powerful and addictive, driven by the release of dopamine in your brain at the sight (and even the thought) of your crush. Dopamine is the chemical responsible for fuelling craving and reward systems. It drives addiction to drugs like cocaine, and habits like gambling.

If you progress past the initial stages of the crush, your brain moves on to releasing norepinephrine (the chemical responsible for obsession), and if you sleep together it triggers the release of oxytocin (the chemical responsible for emotional attachment.)

This is a reason that it can take years to move on from crushes when we’re young, especially in “friends with benefits” and “hookup” situations. Hormones and emotions trump logic, especially if we don’t realize what’s going on.

What Chasing the Wrong Guys Will Lead To

As adults, we continue to crave the same emotional rollercoaster of euphoria and pain we recall from our early romantic experiences. This has become our emotional blueprint, and it is what we recognize and respond to – even if has led to pain, over and over again. We dismiss men who don’t immediately provoke an intense emotional response, in favour of those who do, because that is what we are accustomed to doing.

The problem is that what we are pursuing, and what we will find, is the same thing we found as teenagers – superficial crushes, and dissatisfying relationships. If you stop and think about the guys you crushed on in the past, where do you find each path led you? To genuine love? A great relationship? An experience you’d willingly repeat?

Unfortunately, seeking men who provoke the crush-style desire/reward system that captivated you as a teenager will land you in the worst kinds of adult relationships. You’ll find yourself attracted to emotionally unavailable men who are interested in sleeping with you, but not much else. You might find yourself entangled in a reckless and agonizing romance with a man who is married or taken.

Worst of all, you could fall prey to the narcissist – the man who is charming, exciting, hilarious, and sexy, but remorselessly incapable of loving anyone but himself. He’ll consume years of your life without realizing what it has cost you. He’ll take, with no understanding of how to give back. He’ll expect you to be there when he needs you, but will rarely (if ever) be there when you need him.

And you’ll lap it up, because you’ll think you are earning his love. You’ll believe that one day, he will suddenly see you for the amazing woman you are, and finally give it all back.

But that won’t happen, because he isn’t capable of it. He isn’t evil, he just sees what he wants and takes it. If he stops wanting it, he drops it. You are a handy accessory in his life, and he’ll make you feel special for those moments in which it benefits him to do so. Just special enough to make you believe there’s hope for more.

The truth is that our earliest experiences with crushes, dating, and sex shape our expectations and patterns for our adult relationships. And they can have profound and long-lasting repercussions if we aren’t conscious of them.

Each time we get hurt, it cuts a little deeper, and we lose a little more faith in love. We internalize the pain, coming to believe that either there is something fundamentally wrong with us, or something wrong with all the guys out there. We begin to accept the false conclusion that, because we haven’t found what we’re looking for yet, we’re never going to find it. Our secret, darkest fear is that maybe it doesn’t exist for us.

It is so incredibly easy to fall into the trap of believing that the problem is intrinsic – a characteristic of us, or of them, which cannot be changed. But more often than not, the problem lies in our expectations, patterns, and choices. Things that are simple, if not easy, to change.

How to Stop Chasing the Wrong Guys and Start Dating the Right Guys

If you’ve never stopped to reflect on what desires and expectations are driving your choices, now is the time to do so. If you are exclusively attracted to men that don’t value you, prioritize you, or treat you with respect, it is probably because you’re still trying to work with an outdated model that just won’t work in this stage of your life. You must recognize this and act upon it, to change the direction you are going if you want to end up somewhere different from where you’ve been.

The first change that is within your control is to consciously decide on the type of man you’ll let into your life in future, using logic, not just emotion. Decide what you absolutely do want in a man, and what you absolutely won’t stand for. And don’t make “immediate and irresistible physical attraction” the biggest and only requirement on your list.

If you’ve gone so far down the rabbit hole that you’ve legitimately begun to doubt the existence of good guys, let me remind you – they’re out there. And there are so many of them. This article can help you identify great guys and not-so-great guys, so start with this if you aren’t sure where to begin.

Remember that our task while dating is to weed out the ones who show us right away they don’t identify as great guys. The ones who text but don’t show up. The ones who insist they want to see you but never seem to plan for it. The ones who claim they want to be with you, but vanish at the first sign of conflict.

Saying “no” while dating is even more important than saying “yes.” It’s how you protect yourself from getting used or hurt, and how you preserve space for guys who show you they will treat you well. And remember – the men who do earn a “yes” from you will value it that much more because it didn’t come easy.

If a guy shows you he doesn’t value you, it doesn’t matter how amazing the physical chemistry is between you, or how funny/charismatic/beautiful he is. This is not enough to expect of someone who you will invest your time, energy, and affection in, possibly for the rest of your life.

Over time, good looks stop mattering, physical chemistry becomes routine, and you’ll have heard all the funny stories multiple times. If there isn’t something greater to keep you together, such as respect, trust, intimacy, and tenderness, it simply won’t last. So start expecting more from the men you date, and from yourself in terms of what you’ll put up with.

A well-known piece of wisdom, widely credited to Albert Einstein, says this:
“The definition of insanity is doing the same thing over and over again, but expecting different results”

So right now, I want you to stop and do some soul-searching. Think deeply about what you’re pursuing, and what you’re expecting – consciously and unconsciously – from the men you are meeting.

Try to identify your patterns: the things you do over and over again that determine the outcome with every man you meet. Pay attention to what drives you towards some men, and away from others. Ask yourself whether you’re making good choices, or simply being driven by habit. Make a decision right now that you’re going to try something different next time, if you want to experience a different outcome.

Not sure what to do differently, or how to go about it? In next week’s post, I will talk specifically about the four things you can do to instantly change your patterns, and start attracting better results. Join the Vixen VIP list below to receive future articles directly in your inbox.

How to Find a Good Man: The 5 Key Characteristics to Look For

How To Find A Good Man

In the dating world, it can be tough to know what to look for in a guy.

Of course, we know we should try to find a good man, but we also want someone who is attractive, smart, ambitious, funny, loves kittens, hikes, cooks, measures above 5’8, earns good money, and prioritizes us above all else.

Then we stop and think, “Wow. I’m asking way too much here. It’s hard enough to land a date with a guy I connect with. Maybe I should lower my expectations, and hope for the best.”

Most of our lives we’ve probably believed that “chemistry” (a.k.a. physical attraction) is the foundation of a good relationship. Is it surprising that we end up settling for guys that don’t treat us well, just because the physical attraction was there and the timing was right?

The good news is that we don’t actually need someone who meets every one of our secret requirements to be happy. But we do need to find someone who meets the right ones, and it is crucially important that we know what these are.

There is no single cookie-cutter “good man” out there. They come in all shapes, sizes, and personalities, and each will have his flaws. You likely already have an idea of what traits are important to you, and what attracts you to a man. If you haven’t already thought it out, take some time to articulate what unique characteristics matter to you. Also, identify the characteristics you don’t want in a man.

If you aren’t sure where to begin, I’ve outlined the five key personality traits that, in my experience, consistently distinguish good men from not-so-good men. There are of course many more traits that are desirable in the person you’re dating, but these are the five that cannot be comprised without great risk.

In this context, I define a good man as someone who will treat you well, build you up, and contribute to your happiness on a consistent basis. Deficiency in one of these areas is a serious red flag, which should not be accepted without serious thought first.

The five key personality traits that distinguish a great guy are as follows:

1. Integrity

If a man has integrity, he knows right from wrong and gives a crap about it.

The opposite of integrity is immorality. If he uses people, fails to follow through on promises, or acts with cavalier disregard for the welfare of others, it is a serious warning sign. It indicates he believes other people’s well-being is less important than his own. This man can do immeasurable harm to others without care or regret.

2. Honesty

An honest man recognizes the importance of telling the truth and has the strength to do so, even when it creates discomfort for him.

The opposite of honesty is deceitfulness. If he routinely lies about minor things, doesn’t acknowledge the damage caused by his lies, and refuses to take responsibility when a lie is uncovered, steer clear. Trust is the foundation of a loving and secure relationship. Without it, you will constantly wonder where he really was, what he really thinks, and how he really feels. You’ll never know for sure how much you matter to him, which will condemn you to the worst kind of relationship purgatory.

3. Kindness

A kind man has empathy for others and conscientiously tries to impact the lives of those around him in a positive way.

The opposite of kindness is cruelty. Unfortunately, cruelty isn’t always obvious up front – but there are small indicators to look out for. Beware of a man who calls you names during a disagreement, puts you down in insidious ways, and seems to take pleasure in the misfortune of others. This type of person is not only toxic but downright dangerous – they enjoy hurting others. This is the most important red flag to look out for.

4. Respectfulness

Respectfulness means treating other people as valid and important, even if they have less than you in terms of money, status, or education.

The opposite of respectfulness is arrogance, which is tied to narcissism. A narcissist won’t ask you too much about yourself but will gleefully talk about himself for hours upon end. You’ll notice he never asks your opinion about what you want to do or where you want to go. Be careful of this man, because he loves himself more than he’ll be able to love you. You’ll always come second to his momentary whims, fancies, and desires – which is not the stuff of long-term bliss.

5. Authenticity

An authentic man is self-aware and lives in alignment with his values. He can accept different ideas, opinions, and people because he doesn’t feel threatened by them – he knows who he is, and is comfortable with that knowledge.

The opposite of authenticity is insincerity, underneath which lies insecurity. An insecure man will say and do things just because he thinks others want him to. He won’t stand for the things he says he believes in, and he’ll put others down to raise himself up. He can’t be relied upon to do what he says, or say what he means. Insecure people often have a patent sense of inner discontent, and they don’t understand people who are genuinely happy. As far as he’s concerned, he is not destined for happiness, nor is anybody else – including you, if you continue to see him.

Identifying Good and Bad Traits on Early Dates

On a first date, the presence or absence of these traits won’t be blindingly obvious – you are both on your best behaviour, trying to impress one another. However, both positive and negative traits will reveal themselves little by little in his words and actions, if you are paying attention. And you absolutely should be paying close attention to these things on your early dates. This is when you are in the best position to notice and respond to red flags.

A good rule of thumb at this time is to judge a man’s character and intentions based on what he does, not just what he says. Does he promise to call or text you, but you find yourself waiting for texts that never come? Does he speak openly, or does he act defensive and contradict himself on small points? Does he ask you out in advance and follow through on plans, or does he vaguely suggest “hanging out sometime” and then bail at the last minute when you finally do make plans?

It is important to recognize warning signs early on. Don’t ignore them and hope they’ll go away – they won’t. What will happen is that, after enough time, you will become so attached that judgment and caution fly out the window. You’ll become more willing to excuse or overlook problematic traits because you are too involved to let go. But these flaws will come back to haunt you in future, and by then, it might be too late to make the tough decisions you need to make.

But enough talk about we don’t want – how can we get what we do want?

How to Attract a Good Man

The surest way to attract someone with specific positive traits is to consciously cultivate those traits in yourself. It is well known that “like attracts like,” so try to live your own life in accordance with what you wish to attract into it. If you have high expectations for your future partner, you should maintain equally high standards for your own character.

Beyond this immutable law of attraction, we also know that our perspective defines our reality. A negative perspective very rarely pays off – in fact, you’ll notice that negative people often get exactly what they expect. If you’re expecting to meet jerks and assholes, then that is what you will find.

The onus is on you to control your thoughts and expectations. It isn’t easy, and you must work at it every single day, but you will see the results in every aspect of your life. If you aren’t taking full advantage of this incredibly powerful tool called attitude, now is the time to explore what you’ve been missing. If you don’t know where to start, begin with lectures by Lester Brown and then move on to Zig Ziglar.

Positive people tend to attract positive circumstances and people into their lives. They interact more constructively with others, thereby eliciting more positive reactions and creating an upward cycle that gains momentum over time. This doesn’t mean that nothing bad ever happens to them, but the extent of damage is less severe because they have developed constructive mental habits that help them control the ripple effect of negativity.

Equally important is the practice of good judgment – learning to recognize right from wrong and good from bad as it relates to your life. It also means using your own intelligence and experiences to make good choices, and reject bad ones. Positivity and good judgment make for an unbeatable combination – someone who expects the best and actively creates it for themselves by identifying and avoiding obstacles.

Take some time to reflect upon your own life. Think about whether you have cultivated positivity and good judgment, and whether your attitude will attract the right things into your life. Do you live with integrity, honesty, kindness, respectfulness, and authenticity? Would you be able to give your partner everything that you are hoping he will give you? You don’t have to be perfect, but you do have to try your best, and to keep trying, even after a failure.

Lastly, don’t allow yourself to lose hope. When you feel despair creeping in, turn your mind from it and refuse to let it take hold. Do something that soothes your soul and makes you happy. Connect with positive and supportive people in your life. Work on a hobby or project you are passionate about. Do something that helps someone else, because giving is known to improve self-esteem and gratitude.

In these moments, just focus on being the best version of yourself, and give it time. Trust that you will attract a man who deserves you, and you’ll know how to recognize him when he finds you.

No chemistry with a guy you’re dating? How to decide whether to give it time or let it go

No Chemistry with a Guy

Question: I’ve been on two dates with someone new, but I don’t feel any chemistry. If there’s no chemistry with a guy I’m dating, should I keep trying with him or move on?
– N

Answer: This is a great question, and one that I think resounds with most women who are out there dating right now. We all crave that immediate and powerful connection that keeps us up at night and leaves no doubt in our minds that we’ve found the perfect man. It’s addictive and exciting, and we know from date one exactly how we feel.

The problem is that sometimes we confuse chemistry with attraction, and what I described above is attraction. You can feel a very powerful attraction to someone, and think it is chemistry – but what if that attraction isn’t reciprocated? Is it still chemistry? If you have strong mutual physical attraction, but disagree on most things in conversation, is that still chemistry? If you can talk and laugh with someone for hours, but don’t find them physically attractive at first, is that chemistry?

In reality, chemistry is far from black and white. It is multifaceted, nuanced, and changeable. It depends on when and how we meet someone, where we are in our lives, and what we’re looking for. It can change based on how long we’ve known someone, what their personality is like, and how they treat us. So in this article, I’m going to focus more on what I think the crux of this question is: attraction.

As women, we have a unique ability to develop attraction to someone over time, even when no initial attraction existed. Think about that guyfriend from university or high school; you know, the one you felt zero attraction to at first, but ended up with a devastating crush on six months later. Maybe you hooked up for a while, but it never went anywhere, and you always wondered why.

There are important differences between men and women when it comes to chemistry and attraction. For men, attraction happens instantaneously, and they are driven to pursue it from the get-go. They’ll ask you out on dates, try to impress you, and try to sleep with you – all at a hundred miles a minute. This attraction, if paced, has the potential to bloom into romance, love, and dedication. On the other hand, immediate rejection will not kill the attraction, but it will stunt its ability to bloom into something more – it kills the potential for romance.

For women, attraction doesn’t need to be instantaneous – it is more complex and dynamic. Immediate attraction can fade over time if a man treats you poorly, or if you realize he isn’t a good guy. Similarly, attraction can develop over time as we grow more comfortable with someone, and find their personality attractive.

You are still early in the game after two dates. I wasn’t sure about Daniel until the fifth date, when happenstance was responsible for determining the fate of our relationship. If the weather had been warmer, I would have gone straight home and maybe never seen him again. But it was the coldest night of the year and his place was nearby, so I joined him for one more drink, and everything changed.

But sometimes, a guy you aren’t attracted to is just a guy you aren’t attracted to – and there’s no way around it. If the thought of kissing him makes you recoil, that’s a pretty powerful indicator of your feelings. If you dread the prospect of seeing him, that’s another sign you should listen to.

To determine whether there is potential for attraction to grow over time, these questions will help you evaluate your chemistry:

  • Is he actively pursuing you, and showing interest on a consistent basis?
  • Does he treat you well and make you feel desired?
  • Does he seem to be a genuinely good guy, with personality traits that you find attractive (humour, kindness, intelligence, ambition)?
  • Do you enjoy talking to him and spending time with him on a platonic level?
  • Do you feel any level of physical interest in him?

If the answers to these questions are all “yes”, then I would suggest giving it at least one more date. However for your next date, it is important to ensure that your date involves some sort of adventure. It can be difficult for attraction to develop over dinner and conversation alone – you need to share experiences and activities to bond. An active date can serve to put you both more at ease so that you are genuinely yourselves, rather than being your First Date selves.

Some ideas for adventure dates include going for a hike, or meeting for brunch in the city and then walking around a neighbourhood. You could meet at Spin for drinks and ping-pong, or go to Riverdale Farm and get ice cream afterwards. You could grab some cheese and wine on Queen West, and have a picnic in Trinity Bellwoods park. Or if you are athletic types, you could go for a bike ride along the waterfront path and stop in somewhere for a beer.

Whatever you do, the goal is to choose something that gets you out into the world, moving and experiencing new scenery together in a low-pressure environment.

These types of experiences will help build your emotional chemistry, which has a significant (if slow-moving) effect on physical chemistry. The tricky part is that guys often want to move more quickly with the physical side of things, which is problematic if you aren’t there yet. Sometimes this will cause so much undue pressure that you panic and break it off, simply because you weren’t attracted enough yet to get physical with him.

If you find yourself in this situation, but think he’s a really great guy who you could be attracted to in time, don’t be afraid to let him know that you want to keep seeing him but you need to move slow. He’ll probably be disappointed, but a good guy will respect your request and still want to see you. If he doesn’t have the patience for this, then your decision is made for you – and at no great loss.

During this time I would suggest continuing to date other people, recognizing that he’ll likely do the same, until/unless you agree to be exclusive. Right now, you’re just getting to know each other – you don’t need to jump in feet first. Dating isn’t just romance, it’s friendship-building too – and those bonds take time to develop. If you think there might be potential, then it’s worth a slow burn at first because it can grow into something powerful and enduring.

Remember that the pace of the relationship is always within your control. The moment you stop enjoying your time with him, or develop a stronger connection with someone else, or realize that chemistry hasn’t developed as you hoped, you can end it. For now, just relax, enjoy an adventurous date or two, and see where it takes you.

How to be a Great Date: First Date Conversation Topics and Questions

How to be a Great First Date

Question: I am going on a first date with a guy I don’t know very well. I am feeling nervous because I’m really interested, but worry that I’ll act awkward and won’t know what to talk about. What is your advice for great first date conversation?
– T.

Answer: This is a perfectly normal way to feel before a first date with someone you are interested in. First date conversation is a source of anxiety for almost everyone!

Right now, you are nervous, excited, and obsessing about the best and worst case scenarios for this date. Fortunately, there are tried and true strategies that will help you keep the conversation flowing naturally during your first date, which I will share with you here. I would also suggest reading my article about how to put yourself in the right mindset before your date, so that you can be the best version of yourself.

The very first thing you should do is take some pressure off yourself. Understand that a guy isn’t going to fall for you because of something specific you say or do during a date. A man will like for you for a multitude of reasons that are inherent to who and how you are – your demeanour, attitude, the way you smile, your gestures, the inflections of your voice, and your physical chemistry. You can’t talk a guy into having feelings for you, so that isn’t what you need to do on this date.

Guys are intuitive about their romantic interests, and they usually know in a matter of seconds whether or not they are interested in you. Since this guy has asked you out on a date, you can already be reasonably sure that he is interested in you. Now it’s about keeping your cool and pacing things as you get to know each other. All you have to do on this date is show up looking your best, smile, and try to make your time together light, flirty, and fun.

The best thing you can do is to mentally re-frame the situation as though you are meeting up with a new friend or acquaintance. Any of the big expectations or hopes or fears you might have for this new guy, file them safely away, and try not to think about them.

What matters at this point is that the two of you get to know each other and enjoy each other’s company. Always keep your early dates drama-free. If the potential for a relationship is there, it will unfold naturally in a positive and low-pressure environment.

Dramatic, high-pressure, and intense romances often burn bright and brief. They rarely lead to a healthy and lasting relationship. Instead, the woman usually ends up over-invested while the man pulls away. This leads to painful endings, betrayal, or in the worst cases, dissatisfying dead-end relationships. To avoid these outcomes, limit your emotional investment during the early stages of dating. If this is a challenge that you repeatedly face, I’d suggest reading this article about how to overcome this pattern.

Your early dates should be spent listening, chatting, and enjoying a meal or experience together. You want to ask light and non-invasive questions to get to know him, and to learn what type of person he is. How does he spend his time? What motivates him, and makes him tick? Where does he come from? What are his family and friends like? What books and movies and music is he into? What is he interested in, and what are his hobbies?

You can actually download my free ebook containing 30 fail-proof first date conversation ideas and questions, if you need extra inspiration. It also includes the 10 conversation topics to avoid at all costs on a first date.

This is the time that you should be internally evaluating whether he is a good guy for you to be dating. Once you are physically and emotionally invested, it becomes much harder to make these judgments because rational thought goes out the window. That’s why this is the time to listen as he tells you about what he wants from life.

Pay attention if he jokes about having an addiction (to booze, drugs, porn), brags about being lazy or immature, or tells you that he does or doesn’t want certain things out of life (stability, kids, money, travel, etc.) Men tend to say what they mean, even when they phrase it as a joke. Big picture items and vices are unlikely to change, so if you notice a red flag on the first date, put serious thought into whether it’s something you’d be able to live with if your relationship were to progress.

Of course, you shouldn’t be outright asking questions on these topics unless you want to scare him off immediately! They’re just what you should be listening for as he speaks. I suggest letting the man lead the conversation and ask most of the questions during the first date. He will reveal more about himself, put in greater effort, and feel like he has won you over with his conversational acumen.

Decide in advance to let him say hello first, and allow him to hold the door for you. Let him ask the first questions, and reach for the bill at the end. This will save you the stress and awkwardness of wondering how to act in these moments. It will subconsciously motivate him to try and impress you rather than vice versa.

This type of tension and challenge is appealing to most men, and empowering to both of you. It means you don’t have to panic to fill every empty silence, and you won’t come off as though you’re desperately trying to impress him (which a turn-off for most guys).

Instead, focus on being a wonderful date, and letting the best parts of you shine through. Smile, laugh, and answer questions openly (but without TMI). Be positive, playful, and genuine. Reciprocate questions where appropriate, and occasionally cherry-pick something from the conversation to take it in a new direction if it lags.

If you (or your date) are painfully shy, and struggle to keep conversations going, cherry-picking is a very useful tactic that can help you. Cherrypicking involves paying close attention to little tidbits in each sentence that could lead to another interesting conversation. The key is to try and activate your curiosity – the desire to know more about someone’s experience, or choices, and how they came to be where they are.

For example, you might start by talking about your living situations. He could say something like “My apartment is at Yonge and Eglinton.” You can cherry-pick two things from this sentence:

  1. He lives in an apartment building rather than a house. This is something you can potentially use to branch off into a new conversation: “How long have you been in this apartment? What’s the building like? How did you find your current place?”
  2. He lives in the Yonge and Eglinton neighbourhood. This is something else you can use to branch off into other subjects “How do you like the Yonge & Eg neighbourhood? What made you choose that area to live in? Do you have a favourite restaurant(/café/bar) in the neighbourhood?”

You want to keep your questions and conversation airy. On the first date, don’t ask anything you wouldn’t ask a colleague over lunch. Avoid past dating history, family drama, finances, work grievances, personal tragedies, and illnesses. There’s plenty of time for all that fun stuff later on in the relationship, when he’ll be able to listen with more compassion and genuine care.

If he brings up one of these subjects in a direct question on the first date, keep your answer minimal, and move on to a new subject at the first opportunity. If he brings it up his own tragedy or grievance, listen and be compassionate, but don’t probe too deeply.

Instead, ask him about his interests and hobbies, travel plans and experiences, and what he’s been up to over the weekend. Ask him about the town where he grew up, what university he went to, and how he got into the career path he’s on now. Don’t be shy about asking questions that seem cliché – it’s how you get to know someone new.

It’s okay to ask “so, do you read or are you more of a movies type of person?” and then take it for there. If he’s a movies guy, ask about his preferred genre, or if he’s seen anything particularly good lately. Does he prefer to go to the movies, or to watch at home? Find out his all-time favourite films and actors.

Conversation will stem from where your tastes overlap or diverge – it’s okay to have differences in opinion, so long as you approach them with curiosity, humour, and no judgment. Saying “Oh, I think that genre sucks” will just kill the conversation, whereas saying “all my friends love action flicks too, but I’m a sucker for horror films!’ will create a new direction for the conversation.

Great conversations balance agreement and challenge, with mutual respect and open-mindedness. At this point, you shouldn’t be debating topics that are critically important to either of you (like religion or politics) so it isn’t about winning or convincing the other person to share your point of view. It’s about listening to and appreciating the other person’s perspective, and letting the conversation meander through territory that will be comfortable and non-contentious for both of you.

The last thing I’ll emphasize here is the importance of positivity in these early conversations. Most of us are drawn to people who are happy and confident, so even if you don’t feel this way inside, do your best impression of it. As they say – fake it ‘til you make it.

I know this can be incredibly difficult if you are going through a tough time at work or in your personal life. Hopefully you have a strong network of friends and family, or a counsellor who you can turn to for the support you need. After you’ve been dating someone for two or three months, you’ll be able to talk about these things with them. But the first date is not the time.

On your first date, focus on enjoying the moment and letting go of life’s pressures, so that you can be the best version of yourself, and make the most of your time together.

Advice for a Stress-Free First Date

Advice for a Stress-Free First Date

Many people view first dates as inherently stressful, and have never experienced a stress-free first date. A great deal of anxiety, nervousness, and high expectations can surround a first date, making it easy to psych yourself out rather than psyching yourself up.

However the first date should actually be the least stressful date of all, because you have little to lose and everything to gain. There are certain attitudes and routines that can help you relax and enjoy your date, by reducing stress triggers, minimizing negativity, and focusing on making yourself feel good beforehand!

On a first date, you want to be the best version of yourself – refreshed, happy, and relaxed. You should feel confident and carefree, letting go of stress and insecurity so that you can fully enjoy the moment. To achieve this, there are specific habits to develop (and bad habits to avoid) as well as concrete strategies you can use to prepare yourself for your date.

Let’s start with the day or two before your date. If your date is Saturday night, on Friday night you’d be wise to take it easy – don’t stay out until 3am getting wasted at the bar. You’ll feel tired and cranky the next day, which will affect your mood and confidence on your date. Instead, spend Friday night with girlfriends taking it easy – go for dinner, or have a movie night, but try to be in bed by midnight so you’ll wake up feeling refreshed the next morning.

To reduce your stress on the day of your date, I recommend picking 3 possible outfits the night before your date. Choose three options that make you feel great about yourself – the dress you put on when you want to turn every head in the room, or the killer skirt/blouse combination that makes you feel like you’re starring in Suits. Plan everything down to the shoes, earrings, and purse you will wear with your outfit.

The reason I suggest choosing three outfits is that sometimes, something unexpected happens with the outfit you originally picked. You notice a stain at the last minute, the weather is drastically different from what you anticipated, or your mood just doesn’t fit the outfit that day. It helps to have two pre-picked backups so that you don’t panic right before your date.

The day of your date, keep yourself occupied. It’s a great idea to exercise or do something active, because the endorphin boost will improve your mood and energy levels. So go for a workout or a walk around your neighbourhood in the morning. Meet a friend for lunch, or work on a hobby/project that you love. If you’re the type of girl who likes being pampered, get a manicure and pedicure. Whatever you do, try to minimize the time you spend sitting around obsessing about the date that night.

As evening approaches, start your preparation routine early. Take a leisurely shower mid-afternoon, style your hair, spritz your perfume, and do your makeup. I always do my makeup and hair before getting dressed. For me, it ensures that I feel confident with whatever outfit I put on, since I already look my best. This will also protect your outfit from the ravages of makeup dust and accidental spills.

Strive to achieve a look that makes you feel beautiful without being artificial. You don’t need to wear a mask of makeup, or an intricate updo that won’t survive a gust of wind. Particularly with makeup, it can be very tempting to go overboard. However once you hit the point where you smile in the mirror and feel pretty, stop there! Don’t add that extra layer of eyeshadow or bronzer – too much will just detract from the final result.

As you’re doing your hair and makeup, play music that puts you in a good mood, and gets you feeling ready to go out. I usually have an extra bit of caffeine in the afternoon if I know I’ll be going on a date that night. Instead of an afternoon tea, I’ll have a coffee or latte around 4pm, so that the infusion of energy will carry me through my preparations for the date. There’s nothing worse than slumping into exhaustion an hour before your date, and wondering how you’ll drag yourself out the door and survive an evening of flirting and socializing. Don’t let that happen! Plan for it, and take the measures required to keep yourself energetic and positive.

An hour before your date, you might want to crack open a bottle of wine and pour yourself a hefty glass or two to help you relax and boost your mood. Sip it as you do your makeup and listen to your music. My go-to routine involved a glass of wine while doing my makeup, then a Manhattan shortly before leaving my house. This takes the edge off and primes you to go out expecting to have a good time.

Your attitude and expectations at this point in time are crucial. Many of us developed fairly negative pre-date mental scripts that run through our heads in the hours before a date. You wouldn’t be the first person to think to themselves, “This could be the first date with my future husband and the love of my life! I wonder if he’ll like me? And if he wants kids? Is he a dog person? Should I sleep with him tonight? What if he doesn’t like me? Oh god I better not screw this up! I could ruin everything!”

Alternately, you might have the opposite pre-date script: “Ugh, this is probably just going to be another awkward failed date. I don’t even know this guy. We’ll have nothing to talk about. Besides, the guy I’m really into works two cubicles down from me at the office. I wonder what he’s up to tonight?”

If any of this sounds like what goes through your head before a date, then it is high time for an attitude overhaul. Neither one of these scripts will prime you to feel or act your best on your date – in fact, they’re both likely to sabotage what could otherwise be a great (or at least decent) date.

Here’s how I want you to re-frame your thinking about the night ahead: You are going out to have an adventure tonight. You are going out to make a new acquaintance. To laugh, share a drink or a meal together, tell stories, and listen to stories. To be curious, playful, and have fun together. Tonight, you will meet someone new, and enjoy that moment in time together.

Your date tonight might end up being a one-time occasion, in which case you will have made the most of it, practiced your date etiquette, and will have a pleasant memory to look back on. If you end up having great chemistry, then it will be a great surprise – you’ll have an even better time, things will evolve naturally, and you’ll probably see each other again.

The point is that you are both just curious about each other right now, but that’s it – you have nothing to lose. You already know he is interested in you if he has asked you on a date, so all you need to do is relax, smile, and be your badass self. Tonight, your mission is simply to enjoy the ride, and to be good company for your date. So enjoy a drink or two beforehand, dress to kill, and go out with an open mind, ready to see what kind of experience life might have in store for you.

If your nervousness stems from shyness, or difficulty conversing during dates, then read this article about how to be a great date. You can also download my free ebook containing 30 fail-proof conversation ideas and questions that you can use to generate fascinating conversations with even a complete stranger. It also includes advice on how to put yourself and your date at ease during your date, and the ten topics of conversation to avoid at all costs on a first date.

Should I Date My Guyfriend, or Will it Ruin My Social Group?

Dating Your Guyfriend

Question: What if you’re into a guy in your friendship group, but you don’t want to pursue it due to fear of ruining a good thing with the group? What’s your advice?
– E.

Answer: Realizing you want to date a guy in your social group is perhaps one of the most common dating dilemmas faced by women in their university years and early twenties. Dating someone in your group of friends isn’t always a bad idea, but complications are bound to arise, so it’s important to think it through carefully first.

It is easy to develop feelings for a guy who is part of the group because you spend so much time together in low-pressure situations. You feel like you can be yourself, and you’re getting to know each other on a genuine level, as opposed to trying to impress each other on a date. While I’ve learned that first dates don’t have to be stressful, I’m also well-acquainted with the appeal of a guy who you’ve already gotten to know with zero pressure or expectations.

On the flip side, you also know that any potential relationship will likely have repercussions for the group as a whole, and thereby your social life and other friendships that might be important to you. It’s scary to think that if things don’t work out, you could lose your connection to his friends, or the traditions and habits that you share as a group.

I won’t lie to you and tell you that this isn’t going to happen. In fact, I’ve rarely seen a situation in which this did not happen eventually. However it is important to realize that other forces in life will shape your group regardless of your dating choices. The group will grow, mutate, and divide, no matter what you do. People will come and go, and you’ll grow closer to some and drift away from others.

The group of 5 lifelong friends I had when I graduated from university at 22 was very different from the group of 20 co-partiers I considered my friends in first year. Many relationships formed and dissolved throughout those years, which contributed to the group mutation. In the end, I was way happier with the group I ended up with than the one I started out with – and it was one quarter of the size.

My point here is that your concern for the welfare of “the group” is natural, but shouldn’t be your top priority. It shouldn’t determine what relationships you do or don’t pursue because ultimately, your true friends will stand with you either way. And as any cliché will tell you, these are the only people who matter.

Those who don’t care enough to try and preserve their friendship with you probably won’t add much to your life in the long run. While it may be fun to knock back drinks with them at the bar on Thursday nights, or watch hangover Disney movies the next morning, if they don’t support you they won’t stick around for long. They’ll eventually be replaced by different people who add more to your life.

All this aside, the formation of a new relationship doesn’t usually do any damage to the group in and of itself. If anything, a relationship can bring the group closer together. Even the confession of unrequited feelings doesn’t usually do much damage beyond a few awkward hangouts before things revert to being normal – at least for the rest of the group. Lasting damage to the group usually only occurs in the event of a disastrous breakup where there is drama, anger, betrayal, or a shitty person involved.

This brings me to what is, in my view, the most important question in this situation – what is this guy like, and what is the dynamic like between you two? Do you think (or know) that he is into you too? Has he told you, or made gestures to show you? Most guys will make it clear in one way or another if they are interested, and the only boyfriend worth having is one who wants to be with you.

If the answer is “yes” or “I think so”, then the next questions to ask is how much you trust him. Are you confident that he’s a good person? More on the importance of a good guy (and how to identify one) in this article. Are you sure he wouldn’t try to turn your friends against you if things didn’t work out?

Beyond the characteristics that originally attracted you to him (usually humour, charm, and physical chemistry), does he have the capacity to be affectionate, caring, and generous? Would he be a good boyfriend, as well as a good friend? These questions seem obvious, but they are important, and you’d be surprised how often we overlook them.

Sadly, I’ve witnessed the fallout for women who dated guys in their friend groups that turned out to be emotionally manipulative, cruel, vindictive, possessive, indifferent, disloyal, and the list goes on. You need to be sure you aren’t blinded by attraction, and that you try to see this guy for who he really is.

If you are confident that he’s a good guy who reciprocates your feelings and will treat you like a girlfriend (not just a buddy or FWB), then do not hold back on account of concern for the group. The group will be fine, and you’ll be fine too – your good friends will always stand with you. They’re the core of a group that will morph and change throughout your life, no matter what. You’re just along for the ride, so pursuewhat you believe will make happy.

How to Reject a Guy Nicely

How To Reject A Guy Nicely

One of the most interesting contradictions in the dating world is the balance between the desire to be approached by a guy we’re interested in, and the dread of being approached by a guy we aren’t interested in.

We’ve all sat with girlfriends, drinking wine and asking each other, “where are all the men? Why don’t I ever get approached by nice guys?” And yet, we’ve all been approached guys we’ve had to reject. Maybe the guy came off as awkward or aggressive, or the attraction just wasn’t there. Maybe we’re only approached while in a relationship, but when we’re single we wonder, “what happened?”

To understand this, we first have to put ourselves in a man’s shoes and think about the situation he’s facing if he does want to approach a woman. It takes a great deal of courage (or arrogance, or recklessness) to approach a stranger out of the blue, especially when you know the approach will most likely end in rejection.

Unfortunately, that rejection often isn’t kind or respectful. It’s all too easy to be harsh or dismissive when rejecting a man. Maybe we do it without thinking, or to discourage persistence and thereby minimize our own discomfort.

The problem is that this type of negative response is increasingly conditioning men not to approach women in person, lest they be scornfully and publicly rejected. These experiences create fear, defensiveness, and resentment in otherwise nice guys – they begin to think, why would I bother risking that when I can just open up Tinder and save myself the stress?

For this reason, I always advocate showing the greatest degree of kindness, empathy, and respect possible when declining an approach by someone you aren’t interested in. Assuming they approached you nicely and directly, with a line like “Excuse me, I just wanted to let you know I think you’re really beautiful,” there is absolutely no reason to roll your eyes and walk away, or to say acerbically “look buddy, I’m really not interested.”

It’s just as easy to flash a genuine smile and reply with “That’s so kind of you to say, thank you!” Sometimes men are so taken aback by this response that you can gracefully slip away before next line comes. In cases when they do have a next line ready, (“have time to go for a drink?”) simply look them in the eye and politely say, “it’s so nice of you to ask, but I don’t want to create the wrong impression. I’m really sorry, but [insert honest but minimal reply, like “I’m not dating right now.” Or “I’m not available right now.”] But it was nice meeting you!”

The key is to do three things:
1. Smile and respond directly
2. Acknowledge the compliment and say thank you
3. Politely decline, without over-explaining, and end on a positive note

I view it as preserving this guy for the next woman he wants to approach – a woman who might be more receptive than you were in that moment. Maybe that next woman is meant to be his future wife, and you’ve just ensured that he’ll have the confidence to approach her. She would thank you if she could.

Additionally, you’ll walk away feeling good. Instead of putting someone down, you created a positive interaction, while still being true to yourself. You’ve generated good karma for both of you.

The exception to this rule is when a guy approaches you in a way that makes you feel uncomfortable, disrespected, or threatened. I don’t advise responding at all to cat-calls, negging, comments shouted on the street, or anybody who physically grabs you in attempt to start a conversation. In these cases, the best course of action is to either ignore them completely and walk on, or to tell them firmly to leave you alone.

In time, exercising a kind and genuine approach to rejection will empower you in other ways. You’ll feel less trepidation about the prospect of being approached by guys you aren’t interested in because you’ll know that you can decline in a constructive way. This will be reflected in the level of confidence and openness you project, which will encourage more men to want to approach you, increasing the likelihood that you will be approached by someone you are interested in.

The more often men are declined with kindness and respect rather than scorn and cruelty, the more inclined they’ll be to try again next time. And that is a win-win for everybody.

10 of the Best Romantic Date Spots in Toronto

Salt Wine Bar

Choosing a romantic date spot can be almost as anxiety-inducing as choosing your outfit for a first date. While I typically suggest leaving the date planning to the guy for dates 1-3, at a certain point it’ll be your turn to take him out – be it in celebration of a birthday, a promotion, or just as a spontaneous surprise.

When that time comes, you’ll want to be equipped with a few great ideas for a fun but special date spot. Since moving to Toronto, I’ve dined at hundreds of restaurants downtown, spanning from hole-in-the-wall to hipster to fancy. Below are the ten restaurants that stood out in terms of atmosphere (cozy and romantic), food (unbeatable) and experience. I’ve had some of the best dates of my life at the places in this list!

Check out the menu and prices before making your choice. Most of them tend towards the upper end of the price scale, however are still reasonable for the quality of food and experience they deliver.

  1. Salt Wine Bar
    225 Ossington Ave, Toronto ON
    Iberian/Canadian TapasSalt stands out for the intimate and romantic atmosphere of their space, in addition to their delicious food. The service is attentive and professional, and the wine selection is impressive. If you choose Salt, make sure you try the Cedar Smoked Manhattan, which is to this day my favourite cocktail of all time. After dinner, you can stroll from Ossington Avenue to Trinity Bellwoods Park, perhaps grabbing a bottle of beer or two from Bellwoods Brewery along the way.

    Salt Wine Bar
    Salt Wine Bar
  2. Branca Restaurant
    1727 Dundas Street West, Toronto ON
    Argentine Grill HouseChoose Branca if you want an experience that tends towards eclectic and trendy rather than traditional. The ambiance is busy and energetic, but the service is still on point. Like most Argentinian restaurants, the menu is meat-centric, but the vegetarian dishes on the menu do not disappoint. This spot also works well for double and triple dates with friends.

  3. Portland Variety
    587 King Street West, Toronto ON
    TapasLocated in the trendy Fashion District neighbourhood at King and Portland, this restaurant is elegant, lively, and sophisticated. Their beef tenderloin carpaccio and grilled squid are mouthwateringly delicious, and they offer a selection of unique cocktail creations. It is worth noting that they also have a bangin’ brunch menu and make a damn fine cup of coffee, so it’s a great Sunday morning brunch destination as well. Just make sure you call early to make a reservation.

    Portland Variety
    Portland Variety
  4. Sassafraz Restaurant
    100 Cumberland Street, Toronto ON
    French/Canadian CuisineSassafraz is a more traditionally upscale Nice Date restaurant, located in the heart of Yorkville. It’s the perfect spot to savour a selection of fine cheeses and at least one bottle of nice red wine, before taking a romantic midnight walk together through the neighbourhood.

    Sassafraz Restaurant
    Sassafraz Restaurant
  5. Bar Isabel
    797 College Street, Toronto ON
    Spanish TapasBar Isabel is hands-down my top choice for a date destination at any time, for any occasion. Located in a nondescript building on College Street, marked only by a small neon sign, the inside is colourful and eclectic, warmly lit with vintage lamps. The food is absolutely exquisite – the can’t-miss dishes are the roasted bone marrow, and the sobrasada with foie gras.

    Bar Isabel
    Bar Isabel
  6. Maple Leaf Tavern
    955 Gerrard Street East, Toronto ON
    North American CuisineLocated in a gentrifying neighbourhood in Toronto’s east end, Maple Leaf Tavern captures the stately class of old-school swanky restaurants, and features elevated North American cuisine. I’d recommend trying the burger or the lasagna – both were amazing.

    Maple Leaf Tavern
    Maple Leaf Tavern
  7. Le Select Bistro
    432 Wellington Street West, Toronto ON
    FrenchExpensive, cozy, and upscale, Le Select offers a wonderful experience that feels (and tastes) just like a classic Parisian restaurant. The duck confit was incredible, but you can choose almost anything on this menu and it will be divine. The service is attentive without being overbearing, and the upscale prices will feel worth it for the quality of meal you will enjoy.

    Le Select Bistro
    Le Select Bistro
  8. Dimmi Trattoria
    140 Cumberland Street, Toronto ON
    ItalianThe most budget-friendly spot on this list, Dimmi Trattoria has been a magical experience every time I have dined there. It is a great place to go in the winter, for a hearty meal in a cozy and romantic restaurant. The service is excellent, and every pasta dish I have tried there has been amazing – which is saying something, as my standards for pasta are pretty high. Terroni and Cibo pale by comparison, and also come with higher price tags. Dimmi Trattoria is a great mid-priced restaurant with a high-end feel, and located in Yorkville no less!

    Dimmi Trattoria
    Dimmi Trattoria
  9. The Gabardine
    372 Bay Street, Toronto ON
    Elevated Comfort FoodTiny and lovely, The Gabardine is an unexpected gem located on Bay Street just south of Queen Street. Whimsically decorated with white marble and teacup candles, their menu boasts a concise selection of elevated comfort foods made gourmet.

    The Gabardine
    The Gabardine
  10. Carmen Restaurant
    922 Queen Street West, Toronto ON
    IberianExotic, cozy, and relaxed, this is the place to go to enjoy Spanish paella and margaritas in Toronto. Prices are on the higher end, but it is worth it to take your time and enjoy everything their menu has to offer. Try the fried artichokes for your appetizer – I still lust after them, and it has been months since my last visit. The restaurant is quite large, so expect some rambunctious groups nearby and an energetic atmosphere.

    Carmen Restaurant
    Carmen Restaurant

Having the Talk: How to Go From Dating to Relationship

Having the Talk - Going from Dating to Relationship

Having the talk, and making the transition from dating to relationship, is perhaps one of the scariest milestones of a new relationship.

You’ve realized that you are no longer interested in dating anybody else, and more importantly, you realize that you don’t want him dating anybody else, either. But you aren’t really sure where he stands on the issue, but you dread bringing it up in case the answer is something you’d rather not hear.

For many women, this point comes 2-3 months after the first date (sooner if the relationship has moved very quickly). If nobody has broached the topic of exclusivity, the tacit assumption is that both of you are still discretely dating other people. However you have steadily been losing interest in other guys, and becoming increasingly emotionally invested in the relationship you are building with this person.

Occasionally, the talk arises organically, early in the relationship, but this depends on the personality of the man you are dating. Some men are more passionate and possessive, and as soon as they realize they have feelings for you they will make it clear they want exclusivity. Other men are content to move at a slower pace, hinting at their feelings but waiting until the woman raises the subject.

I consider this moment to be the final stop before the point of no return. It is a delicate, excruciating moment, the outcome of which can define the next chapter of your life. There is a proper way to handle this conversation, but first I want to look at two common mistakes that are easy to make at this point in time:

Common Mistake #1

The first, and arguably most common, mistake is to withdraw into yourself, becoming insecure and anxious. Acknowledging that you have strong feelings for someone makes you vulnerable, which can cause you to panic and try to protect yourself in response. You over-analyze the situation in your head and with your friends, and idly envision all the possible negative outcomes of the conversation you need to have.

Instead of trusting him, and trusting yourself to handle the conversation, you obsess internally, trying to read his behaviour and his thoughts in an effort to detect whether he reciprocates your feelings. If he unknowingly fails to give the signs that you hope for, you start to resent and distrust him. You feel annoyed when he takes too long to answer your texts, become paranoid about his intentions and behaviour, and begin to convince yourself that it just isn’t going to work out.

The problem with this approach is that it can sabotage an outcome that would otherwise have actually been positive. Although you might not realize it, this type of internal fear, anxiety, and negativity manifests itself in your behaviour and the emotional energy you project.

Men, although often teased for lack of sensitivity, can actually be very astute to changes in body language, vocal tone, and response from you. Although he likely won’t know what is different or what has caused the change (he might not even recognize it consciously), he will respond by reflecting this energy back to you. He’ll text less often, act more guarded during interactions with you, and seem less excited about your time together.

The relationship will disintegrate, perhaps quietly and without explanation, or perhaps explosively, with a series of escalating arguments over minor things. Either way, this is not the outcome we want!

Common Mistake #2

The second mistake is to take the extreme opposite approach – to completely stifle your desire for an exclusive relationship and pretend that you don’t want anything serious, even as your feelings continue to grow more intense.

The three month point comes and goes, and neither of you have initiated the talk. You continue to spend time and sleep together, maybe even meeting each others’ friends, but you never quite getting to the point of calling each other boyfriend or girlfriend.

Six months pass, and you are now completely in love with him. You still haven’t had the talk, but you silently hope that he feels the same way you do. You ignore any signs to the contrary, and convince yourself that if you continue to play it cool and go along with the “casual relationship” farce, he’ll eventually realize he’s in love with you.

By now, you have passed the point of no return. If you finally raise the subject and find that he doesn’t see the same long-term future that you do, you will be devastated. So, you push these worries to the back of your mind and try to just enjoy the moment.

I’ve seen women led on for years in situations like this. Take Kim for example – she’s gorgeous (think Olivia Wilde), fun-loving, and a great conversationalist. I met Kim when she had been dating a guy for about four months. She was crazy about him, but steadfastly trying to maintain the “cool laid-back chick” attitude.

At 32, Kim was ready for a serious relationship, and certainly wanted exclusivity with him. But she found that whenever she broached the topic, he subtly discouraged her. They continued sleeping together and hanging out, but he was still actively dating other girls on the side, and declining to join her for cottage weekends with other couples.

Eight months in, she finally brought up the topic of exclusivity, only to be told that he wasn’t interested in being exclusive or in having a long-term relationship with her. He said he would still like to date her, but that’s all.

Despite the devastation she must have felt at this point, she was so deeply invested emotionally that she wasn’t willing to cut her losses and move on – she continued to see him for another three months, hoping he might change his mind.

Finally, he did the right thing and ended it himself, recognizing the pain she was in and her inability to walk away. Not all guys are this honourable – some will string a woman along for years if they can (which I discuss in this article, for those of us who are inclined to want what we can’t have.)

So what should you do when you reach the last stop before the point of no return?

The Right Way to Have the Talk

The moment you realize that you are so into a guy that you no longer want to date anybody else, you must acknowledge that it is time to have the talk. People make a big scary deal out of the talk – I’ll admit I’ve been doing it in this very article! But the truth is it doesn’t have to be that way.

If you’ve been dating for three months already, with him in the lead for the majority of that time, chances are good that he is ready to move to the next stage. You should remember that by the third month, the guy you’re dating knows how he feels about you and has already decided whether he sees long-term potential.

If he has decided that he doesn’t see long-term potential with you, literally nothing you can do will change it. The only thing that might be affected is how long you are strung along in dead-end dating. However if he has decided he does see a future with you, this conversation isn’t likely to change that either – so long as you can keep your cool before and during the conversation.

So, the first thing you need to do is turn off any insecure and negative self-talk that creeps into your mind when you acknowledge the need for this conversation. Of course you’ll have fears and doubts, but dwelling on these will only sabotage you. Instead, you must consciously focus your mind on positive outcomes. Envision as many different positive outcomes to your conversation as you can. Picture the words you might say, and imagine yourself maintaining a happy, relaxed demeanour throughout.

Consider the setting and timing for your conversation. You want to choose a time when you will both be feeling relaxed, comfortable, and happy – preferably a Friday evening or a Saturday. You should have it in a setting where you will be comfortable, fairly neutral, and where there is a reasonable amount of privacy.

I think one of the best settings for this conversation is in a park near your house – this way, you are in neutral territory (as opposed to one of your homes.) A park offers a relaxing and positive environment, with ample privacy.

In my particular case, it happened at 2am in a Toronto dive bar called the Silver Dollar Room, after seeing Bleached. We were both giddy from beer and dancing, so when we plunked down in a dark corner holding hands, it seemed natural to turn to him and ask, spur of the moment, “Am I your girlfriend?”

Of course, I had planned to ask this in quite a different way. But when you have the confidence and inspiration to ask in a spontaneous moment, you should go with it. The key is that you shouldn’t wait too long, to the point that you’re hopeless/angry/resentful, or to the point you are so emotionally involved that you can no longer walk away.

You need to time this early enough that, if you receive the response “I’m really enjoying hanging out with you, but I don’t want a relationship right now,” you’ll still have the strength and self-possession to walk away – with your dignity still intact.

Above all else, do not stick around thinking that another three months will change his mind, because it won’t. The kindest thing that he can do if he doesn’t see a future with you is to tell you that honestly. The kindest thing that you can do for yourself is to hear him when he says it, and believe him. It can be devastating, but it also saves you from wasted time and added pain down the road.

If the conversation goes well, which it probably will, then that’s that – you don’t need to push the conversation further at this point, or revisit it again any time soon. Just smile, savour the moment, and enjoy the rest of your date!