You didn’t make the move when you had a chance… now what?

Dear Jack and Jill: I shot my self in the foot with a friend who seemed to like me. I’ve been friends with her for about a year, then she had a boyfriend, and then after the boyfriend was gone and she was clearly flirting with me, I missed a number of key opportunities to make a move. After that she stopped flirting with me. Now I don’t know what to do. Did I miss out on a good thing or is there still a chance for me?

No Name or Address Given

Jill: Sounds simple, but there’s really only one way to find out. You gotta make that move. Sure, the moment may have passed, but putting it out there allows her to know that you actually are interested — which, since you failed to make a move when she put herself out there — she may not even know. Sure, she may turn you down, or the timing may be off, but you’ll be giving her the go-ahead to return to the idea if and when the time is right again. Go for it.

Jack: Not to worry, guy. You can’t really ruin a relationship you haven’t had yet. In the same way that you don’t have to refrigerate mayonnaise until you open the jar ... sort of.

Anyway, the thing is this: there are two reasons a woman might flirt with a man. Either she was really interested in taking your relationship to a different level or she felt safe flirting with you because she only saw you as a friend and didn’t think you’d follow up on it. That means there are two reasons she might have stopped: Either she thinks you aren’t interested or she sensed you are and she doesn’t want a romantic relationship.

The good news is that you have a close personal relationship with her already. The bad news is that you must rely on that relationship and ask her directly if she has any romantic feelings for you. It’s risky but hey, buck up man. Chicks really like it when you’re direct with them. And if you think about it, it’s less embarrassing than making a move on her if you’re wrong about her feelings.

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