Going from friends, to dating, then back to just friends.

A woman's perspective on how to handle the friend - lover - friend transition.
Ask A Woman:  How to handle breaking up with a friend.

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If I have taken a girl out two times and have decided that I’m not that into her.  Do I owe it to her to sit her down and tell her that I’m not pursuing her anymore?  Also, for a little background info, we were friends before we started dating.  If I have to sit her down, what do I say?

– Andrew


Hi Andrew,

Got yourself into a bit of a pickle, eh?  Ugh, is there anything worse than telling someone you no longer want to date them?  Well, maybe hearing that someone no longer wants to date you is worse.  Or at least equal.  Love stinks.

This and that. Not so easy.

If you had not had a prior friendship, I’d say no, you don’t have to sit her down and tell her she repulses you.  It’s only two dates.  You can just let things expire…assuming she doesn’t contact you again.  BUT, if she called you again, then you’d want to, first of all, take the call, but then say something along the lines of “I had a nice time but you oughta know that I don’t think this is going to work out, so I wish you the best.”  And yes, no matter what you say in that scenario, it will always sound just that lame.

Your situation, my friend, is made complicated by the fact that you were/are friends with her.  You need to seek her out and tell her you think friendship is better than romance for the two of you.

You also need to be prepared to lose that friendship, either because she’s got an achy, breaky heart, or because it ends up being awkward for both of you.  And yes, this can happen even after only two dates.  Sometimes the dip into dating means the friendship can’t be salvaged.

As for the nuts and bolts of what you say…be honest–to an extent–with her.  For instance, there’s no benefit to telling her that after seeing her up close during a make-out session, you realized you find her very unattractive.  But you can say something like, “I’m just not feeling a romantic spark with you.”  It’s the truth, but it’s not the whole truth, you know?  Or if you’ve discovered that all she wants to talk about is her teacup Poodle and how many calories she eats in a day, you can go with, “I don’t think we have enough in common.”  Because if you full-out lied and said, “I realized that I just don’t have time do date right now,” and then she heard it through the grapevine that you’re seeing someone else, she’s going to be upset.

I don’t envy you your task, Andrew.  Good luck.  Bye, bye, bye.


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