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.


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