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!


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