Buckle up, cause it’s a long one. I, 25M have known my best friend, 23M for about 7 years now. We met at work, and given that we were the only two guys working in our store, we became close pretty quickly. We have the same sense of humor, we both love exploring nature, and overall balance each other out (he’s very extroverted and I’m very introverted). We’ve always been playful and sarcastic with each other, and we spend a lot of time together to the point where I’ve been asked if we’re secretly dating. The idea had honestly never crossed my mind before, so I always laughed it off. But recently, something seems to have shifted that’s making me question everything.
Now, something I should mention is that I’m bisexual, but I’ve never actually told him. Why? I’m not sure. I guess it’s more due to the fear of losing yet another close friend, which is something that has happened in the past, and given how close we are, it’s not something I’d be able to just brush off. He’s what you would think of when you think of your typical straight guy: always flirting with girls, extremely into cars, has had a few girlfriends and flings in the past, you know the type.
A few months ago, we were just chilling in his backyard together, talking about anything and everything when he randomly brought up his dating life. He expressed his frustration with the fact that he couldn’t seem to find the right girl, despite trying his best. I, jokingly, said that if he wasn’t such a difficult or picky person, he would probably already be planning his wedding. He then says that he can’t seem to find someone who he genuinely wants to spend time with, and then he chuckles and has the audacity to drop the bomb that so many guys do not want to hear come out of their straight friend’s mouth: “if only you were a girl”.
Naturally, I laughed and said something dumb like “Yeah, and even then you’d be complaining” because what else was I supposed to say? My brain had short circuited, but thankfully we kinda laughed it off, changed the subject and that was that. I had honestly forgotten about it until a couple of weeks later. He was getting ready for a date with this girl he was talking to, and since he has no sense of fashion, he FaceTimed me for help. He genuinely seemed excited about his date (at a nearby ice cream shop). About 10 minutes before he was supposed to leave, he gets a message from his date telling him how she wasn’t really feeling it anymore, and said something about how she thought she was ready to date but wasn’t. Since we were on FaceTime, I saw his face go from being super excited to absolutely crushed in a millisecond. I told him the typical “her loss” kind of stuff, and after a few minutes, he said he was still down to get ice cream, and asked if I’d go with him. I, of course, said yes.
As we were eating our ice cream, he again said that he didn’t understand what he was doing wrong, and why some girls would bail right before their dates. I told him that he was doing nothing wrong, and that it wasn’t his fault that they couldn’t see the genuine and down to earth guy he was. I told him that most of the time, finding the right girl took a while and that it sometimes happens when you least expect it. This man, looks me dead in the eyes and asks “Dude, how are you still single?” Confused, I said “Who’s asking?” To which he says “No, I’m being serious. You always know exactly what to say. You’re definitely the type of guy who would 100% treat a girl like she’s the most important person in the world, would definitely spoil her and would absolutely do all these super romantic gestures. So like, why? I mean, what’s not to like?” All I really said was “Idk, I guess I just haven’t found the one who likes me enough to try.” To which he shakes his head and says “That’s crazy.”
After we finished, he looks at me and says “Maybe I don’t need to look for someone to have a connection with.” This got me thinking back to what he had said weeks before, and naturally, because I had this seed planted on my mind, I started thinking more about the what if’s. I think he has too, because after that he no longer talks about wanting to find the right girl, he’s gotten more touchy (playful shoves, grabbing my arm for no reason), and the line between teasing and flirting seems nonexistent at times. (I’ve seen him flirt before, so I know what that looks like and this is definitely that). We’re always at each other’s place, and because of this, I sometimes tend to cook for us (yes, I know how this sounds but a man’s gotta practice somehow). We stay up late watching movies, we spend countless hours playing Mario Kart, and we’ve been going out a lot more often than before.
It’s been a few weeks, and as fun as it is, neither of us have directly talked about this. What should I do? Am I totally misreading this whole thing or should I bite the bullet and ask him? We’re hanging out on Monday night and I don’t know if I should just let it be or bring it up.
TL;DR: My best friend has been dropping hints that he might see me as more than a friend, but doesn’t talk about it. Should I bring it up or leave it alone?