One of my best friends in the world is a guy. We met in high school and 15 years later, we're still close. We've never dated, never talked about it, and it's never really been a consideration for either of us (I think.) I have noticed that he generally finds something to dislike about guys I date. A couple months after my ex and I broke up, we were out, drank a good bit, and he kissed me. I didn't really acknowledge it later because I've always been scared that if a relationship with us failed, I'd lose him permanently and the wounds from my breakup were still pretty fresh. A few weeks ago, we were hanging out and I kissed HIM. Again, neither one of us has talked about it and conversation has been a little stilted for the couple of weeks. I have no idea what's going on! I'm scared to ask about it because I'm worried he'll just say it's not a big deal and blow it off or he'll say it was a mistake. I do care about him and there's probably not many people that know and understand me better than him, but I don't know how to approach this.

The other potential issue with it is one our other girlfriends. She also regards him as her best friend, but she's very, very territorial about it. I've met and been friends with some of his ex-girlfriends before, but she's been hostile about them. I'm afraid that if he dates anyone, especially me, she's going to be nasty about it. There's no history between them and there never will be, but I'm not sure she understands that. (Look, to explain it in detail...there's no way to not sound mean, so just believe me on this one.) She admitted to having a crush on him years ago and swears that's not the case now, but no one is really buying that.

I guess it's just taken a long time for me to get here. Having feelings for him is a really different and new thing for me and it's a bit uncharted. Sure, I've dated guys I had been friends with first, but none THIS close. Of course there's a fear of rejection, but I feel like there's more on the line.