Dear 100 Hour Board,
I have a guy friend who I've liked for a long time; we met at BYU and became quite good friends. I've dated a few other guys, but he's the only one I've ever actually really liked (sad but true). It's become apparent that I'm not going to just "get over him" any time soon.
It's been years since we've lived in the same town (we now live ~2,500 miles apart), and we pretty much only talk/text once a month or so; sometimes less, sometimes more. I live really close to his parents, and he lives really close to some of my siblings, so we see each other sometimes. I'm quite sure that he wasn't interested in me back at BYU, as he only ever asked me on a couple of casual, group dates, and sometimes I think I'm dumb for still thinking it could possibly work out, but then sometimes he'll say something super flirty. And he initiates at least half of our conversations, so he is, at the very least, pretending to like to talk to me. I've come to the conclusion that unless I say something, I will waste my entire life wondering "what if," and have decided that I'll just bring it up over lunch the next time he is in town visiting his parents. How on earth am I supposed to bring this up, though? Do I just say, "Hey, I like you?" I thought about trying to hint at it the last time we met up for lunch but I chickened out. Any advice on getting through what is probably going to be the most awkward conversation of my life? I would also appreciate any advice on how to make it less awkward if he doesn't feel the same way, as I'm friends with his siblings and I can't just avoid him for the rest of my life. Thanks
-Just a girl
First of all, I just wanted to say that I know that "what if?" feeling, and it's the worst. That feeling is the entire reason why I tell anyone who will listen that a polite rejection is infinitely better than ghosting someone or coming up with some lame excuse, no matter how painful or awkward it may be to tell someone no.
Here's a question for you to reflect on: Do you think you would get over him if he wasn't interested? I know you said that you aren't going to get over him any time soon, but if knowing with complete certainty that it would never happen would help, then I think you should definitely tell him how you feel. I really can't help you on how to bring it up, and even if I pretended to know you shouldn't believe me, because nothing I've done so far has worked out, but you should come up with a way that feels right to you.
As far as making it less awkward, these conversations are only as awkward as you make them. As long as you don't make it sound like you can't stand being friends with him if he doesn't feel the same way, everything will be fine. If he isn't interested, just act like nothing ever happened. You can keep being friends (unless he's totally weird about it, but then it's his fault), just never bring it up again. If he doesn't know what to say, just give him all the time he needs to think about it, and let the ball stay in his court until he reaches out to you again. If he does like you that way, congratulations!