Okay. So here is it: I really like my best friend and he’s dating someone. We are best friends, talk all the time, we met about a year ago and lately, it just feels different. I definitely didn’t intend on this but I’m pretty sure I want to be with him and I think he wants to be with me too. But he has a girlfriend so every time we end up talking about it it’s always one big joke like “major in another life” and nothing serious. Do I go for it? I am super conflicted because I was trying to put him back in the friend category and then last week he kissed me. Like what? Should I put myself out there to see what happens? HELP ME!
First, your friend is not treating you like a friend. Sure, he is in a tough spot, but that doesn’t mean he gets to lead you on and then laugh it off and go home to the security of a girlfriend. Life is happening right now, there’s no “another lifetime” mentality. What he’s doing, frankly, is cowardly. It’s the definition of having your cake and eating it too. He gets a girlfriend, a best friend, and a fantasy, and what do you get? Led on, hurt, and left wanting. You’re worth a lot more than that. You are worth more than his manipulation.
What you need are boundaries. You need to tell him, next time this comes up, to knock it off. Is he going to date you? Is he going to leave his girlfriend for you? No? Then you are in no way obligated (and should not) commiserate with him. As I said before, life is happening now. There’s no “missed opportunity” when the opportunity is right in front of you and actively available. If he wanted to date you, truly and deeply, he would. You would make it work because that’s what you do when you love someone. You two seem to have a very solid “friend” foundation and it’s not like he would be leaping for someone he just met, this is someone that he knows as a friend and clearly, the two of you connect. I’ve talked about this sort of things before in this post and think it applies here.
Falling for a friend and having that turn into something wonderful absolutely can and does happen, but remember that he’s not just your friend, you are his as well. Meaning that while you two are viewing your friendship through different lenses you are both experiencing the same interactions. If he thought there was something there he’s able to pursue it. The idea that you have to put yourself out there first so that he feels safe enough to tell you how he feels is ridiculous. You are both adults and if he wants you he shouldn’t need a safety net to go for it. Is that how you’d want him to be motivated? Do you want someone who plays it safe, or someone who would go for it?
Get some space from him and ask yourself if he’s someone who could actually give you what you need. To me, it seems like he’s not meeting you halfway in the friendship and wouldn’t meet you halfway in a romantic relationship either.