When do you stop trying to make it work?

Dear Lisa,

I just dated a woman for a month, but now it ended. She really liked me, and freely expressed it. I had some feelings for her but they were not strong. I mentioned this and that I wanted to see if it would grow, but then she ended it. Should we talk, or go our separate ways?

–Talk It Out (♂ Victoria)


Dear Talk It Out,

Before I answer your question, I want to get into how this situation might have come about. I imagine knowing that your lady liked you so much more than you did her, must have made you feel that you owed it to her to be completely honest about where you were at. Sorting out feelings early on in a relationship is difficult especially with the pressure to start relationships out ‘right’ – as open and honest as possible. But, the fact that you weren’t completely sure if she was the one for you, or if your feelings were strong enough is irrelevant if you have the simultaneous desire to see if your feelings will grow. I know that it feels like lying, especially when she’s so smitten, but everyone, to a certain degree, especially at the beginning of a relationship, is waiting for that magical spark that means the potential for a long term relationship.

More importantly maybe, is that it is quite common for men especially to feel uncertain for longer than their feminine counterparts at the beginning of the relationship. There are many reasons for this, but a large part of it is because identifying feelings for the masculine is more of a skill than a natural gift, where feminine people tend to be more or less readily present to their feelings. The conflict you were having was very real, but it’s not dishonest to keep it to yourself until you’re sure.

Why would you want to keep it to yourself until you’re sure? Let’s begin with the masculine/feminine polarity of intimate relationships. By admitting that you aren’t sure of your feelings may have had a couple of consequences. The first is that, like it or not, the feminine seems to look to the masculine for his certainty and stability, and by telling her your process of working out your conflicting feelings for her, you are, in a sense, breaking the proverbial 4th wall. In other words, you are showing her that you are more human that most women would like to believe. Now, it’s not that this shouldn’t be done in a healthy relationship, but depending on her expectations, she might have felt very unsafe with you once she perceived your struggle and may not be ready to face the fact that men have emotions and feelings too.

Secondly, because the feminine is more prone to insecurity, and depending on her own self worth, your words might have sounded to her as though you said ‘I’m not sure if you are good enough for me, so until I see that you are, I’m letting you know that you’re on probation.’ If that’s the case, breaking up the relationship might have been a better way of dealing with the perceived rejection than switching on her ‘best behavior’ to try and fix things. Nonetheless, it is hard to un-hear someone you care about echo the unsightly things you believe about yourself.

Now, as you probably already know, I can’t really answer your question for you, but I can suggest that you do what will bring you both the greatest peace. To know what is best for both of you, you need to take some time to get clear about your feelings for her. You need to examine your motivations for talking to her: look back at the relationship with an awareness that you have just broken her trust. Maybe part of the reason you want to talk is because you want to fix what she thinks of you, or maybe you just want closure for yourself around why she decided so quickly that it was over. Or, you might come to the conclusion that you really do want to be in a relationship with her. If your motivation is anything but the latter, I would seriously consider walking away – you wouldn’t want to wake up one day six months from now after earning her trust back, and realize that you are going to have to break it to her, for a second time, that she’s not the one for you (you know that fear will always be in the back of her mind). Whatever you decide, you will feel most in integrity when all is said and done if the solution is the best one for both of your hearts.

– Lisa



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