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Dating a Male friend I rejected before

Published on August 2, 2012 by geekneeiab

I’m interested in dating a male friend. We met in college but were never really close and reconnected a year ago purely as friends. We’ve known each other for 10 years. We started hanging out platonically a lot the past year and he used to live two hours away so he would drive from far away to see me. I thought nothing of it. Then he moved to my city and we were close to each other now. One night we went out and he made a move on me. I froze. And we pretended he didn’t try to kiss me. This was three months ago. We kept hanging out then, pretending nothing had happened, me sending mixed signals, both of us casually dating other people. But I recently broke off casual dating because I realized I had strong feelings for him but now I wonder if it is too late? I still spend a lot of time with him and I don’t want to emasculate him by not letting him make the first move. He’s a macho type of guy and I’m trying to apply EMK’s philosophy in his book to embrace being the girl and do nothing, let him come to me. But I feel like that advice applies more to strangers dating versus friends potentially dating. We recently got back to a great momentum where it isn’t weird after all the mixed signals, we’re having a good time hanging out and enjoying the present and I feel like I am ready to tell him I wasn’t rejecting him when he initially made a move on me but was just scared and surprised. So should I make a move (physical or verbal) or will that emasculate him? And if we do date? Do the same rules apply? Should I wait to sleep with him? Because I feel like we already have been on 100 dates (platonically), so I don’t feel weird about sleeping with him sooner if he were ready to commit etc but I guess that is more of a down-the-road concern? Now I’m just freaking out on how to exactly let him know I like him but not nudge or nag or pressure him.


Say to him (perhaps with a bit of a shy, demure tone), "Mike - remember when you kissed me back then? I won't freeze this time if you kiss me again" This way, YOU aren't making the first move, you're inviting HIM to make the first move (AND you're telling him you haven't been able to get that first kiss out of your mind). If he doesn't immediately kiss you, he's either no longer interested in you or he's hopelessly dense and nothing less subtle than a sledgehammer has a prayer of getting a clue through his thick skull.

By the way, don't get TOO worried about turning him off by being too forward - one of the biggest complaints we men have about women is that we wish they'd be more direct and say what they want rather than dropping hints and asking us to read their minds. It's a RELIEF (and a damn flattering one at that) to have a woman clearly state her desires.

If he asks you why now and not then, tell him what you've said here. You froze because his kiss caught you by surprise and scared you, and you needed time to get your head clear and think because you have known him forever. Now that you HAVE had time to think, you realize that you really like the idea of getting romantic and that you DO have strong feelings for him.

As far as when to sleep with him, don't feel any need to rush into it. Hanging out together as friends is NOT the same as dating romantically you should wait and see how things develop between you as a couple before you have sex. You two may well feel comfortable moving on to sex fairly soon, but don't do it until you BOTH want to. It's easy to have miscommunication precisely BECAUSE you have been (platonic) friends for so long and assume he'll react a certain way. I have a hobby that lots of people pick up on their own before getting lessons and training from a professional. The trainers universally HATE getting self-taught people for the first time because they've developed bad habits or learned things that are simply wrong that the trainer has to UN-teach them before he can teach them the right way.

Good luck