There is this guy I like, I have reason to think he may like me too but we’re both playing dumb, or maybe I’m just imagining it all.
Yes, that’s how immature I am. Now please help me.
We’ve known each other for years and we seem to get close to each other, then we take distance, then close again, repeat, repeat, repeat.
I’m terrified of losing him as a friend for trying to be more than just that. I’ve already lost people for showing my interest and I’ve also had to burn the bridge with guys who wouldn’t give me space or kept hitting up on me repeatedly. This happens.
I would like to create a consistent, regular conversation going on. I’m afraid of overwhelming him so I don’t even know what’s a good frequency to reach out.
Personally the biggest challenge for me is finding ways to deepen our conversations. Things tend to stay pretty much on the surface most of the time, even though we can talk of almost any topic openly. Another barrier is our very different interests, we have almost no shared media in common (different music, different shows watched/liked, different videogames liked etc).
Usually when talking to other friends, conversations tend to naturally steer towards more meaningful topics. I don’t know if I’m inadvertently holding myself back with him, or if finding meaningful topics has always been a thing started by the other person and I’ve never realized it.
So, any tips?
Have you got ways to deepen conversations?
Guys, have girls ever impressed you positively and how?
Thanks
I never had much luck dating, tried shooting my shot with a handful of female friends I thought I was getting vibes from, never even got a first date, but stayed friends with them.
The only 2 times I successfully ended up dating someone, the girl took the initiative and kissed me first.
First one was someone I’d just recently met, didn’t really pick up on any vibes, maybe she was putting out a ton of them and I was too much of a dumbass to pick up on them, I just thought she seemed cool and wanted to hang out with her, didn’t really have any romantic intentions in mind. Then she kissed me, I kind of had to quickly rewire my brain and I decided “ok, let’s see where this goes.” Didn’t work out long term, but we had some fun for a while. I did not stay friends with her, she got kind of weird towards the end, and I found out years later that she was very likely cheating on me towards the end, I wasn’t my best self at the time either but I wasn’t a cheater just a stupid teenager, I tried to leave the door open to remain friends but she wasn’t having any of it.
The second time I’d been friends with her for a good long while, again, no romantic intentions on my part, she was cool, we hung out mostly with other friends, sometimes not. She kissed me as we were both leaving a party at the same time getting into our own cars. Really short circuited my brain a little and could not make sense of it. Kind of had to take a day to process it and talk to her to confirm that we were gonna try it out and see where it went. She’d apparently been laying on the flirting extra heavy and I picked up on absolutely none of it. I ended up marrying her, coming up on 6 years married and close to a decade together.
For a 3rd data point, there was a girl I really liked in high school. I’m pretty sure she was flirting with me pretty hard, and several other people even told me in pretty straightforward terms that she liked me. Never quite got out of my own head enough to make a move beyond some clumsy, mostly-joking-but-not-really flirting. I think I was kind of waiting for her to make it clear to me what she wanted in an unambiguous way, and she never quite did it in a way my brain interpreted as an “all systems go” signal.
For some context, the first time I was about 18 or 19 years old, and I started dating my wife in my mid 20s, my failed attempts were all scattered around my early 20s. I’m probably a little neurodivergent in some way, some very mild degree of autism if I had to guess, and depending on who you ask I’m either a shy extrovert or an unusually outgoing introvert (the bit in Clerks about Randall hating people but loving gatherings resonates with me.)
I think the takeaway here is to go for it and don’t beat around the bush. Keep an open mind that he may not be into you that way, but that means he doesn’t want to lose your friendship either. If it’s going to happen, one of you needs to make a move, and there’s a chance that he’s just as stupid as I am and hasn’t even really considered you romantically but if you force his hand he may go “oh shit, yeah, that sounds like a great idea, why didn’t I think of that”
And even if stuff does implode, it doesn’t work out, and you don’t manage to stay friends, it’s probably better than spending the rest of your life wondering about what could have been. I love my wife, wouldn’t trade her for the world, and I’m confident that there’s no one in the world who would be a better match for me, but I do wonder sometimes what sort of fun I could have had with my high school crush, even if it wouldn’t have gone anywhere long-term. A couple weeks, months, or years of fun times would have been worth it. With the other girl I dated, even though things didn’t work out, and I think we mutually dislike each other now, I still think fondly of the times we had together regardless of the unpleasantness that came after, if I got stuck in a time loop and ended up back then, I’d still date her even knowing it wasn’t going anywhere.
Unfortunately I have no particular tips for improving conversation. Somehow I seem to do alright, but I couldn’t, for the life of me, explain how I do it.
Thanks. I appreciate knowing first hand from a guy who didn’t make the first move AND still got to stay with her for a long time; all other stories of girls making the first move I’ve heard either don’t work or end in very short term relationships.
I think I’m not being demonstrative enough, and he probably thinks I’m not interested. There is enough reason for that. But it could also be that he’s not wanting to commit to anything so he’s not asking me anything. I dread this second option. I’m rambling already. What I’m trying to say, in response to your account of not getting the flirts, is that there was some flirting on both sides but also plenty of mixed signals.
I’m a man, my wife made the first move, and I’m very glad she did! Taking the step from friend (or even just acquaintances) to more is risky for anyone. But, and maybe I’m biased here, I think it’s currently even more risky for guys. Word can get around, and you’re more likely to not just lose the one friendship, but to be labeled “creepy” generally if you’re wrong. Of course it’s possible for that to happen to a woman, but it’s way less likely for a woman to be perceived as a creep in general, and also men don’t talk amongst themselves the way women tend to.
Anyway, I knew my wife from a social space, and I didn’t want to be the guy who poisoned the environment and made it an uncomfortable location for women by pursuing any of them. So I was friendly and tried to be as non threatening as possible, which meant no asking out. So I was very relieved when she made a move!
Don’t know if your situation is anything like that, I’m just unsure of your source that says “active woman means short term”. I mean, think of all the dudes hitting on strangers in bars which either turns into a one night stand or a short fling. The averages have got to be better than that, right?
Thanks. I don’t know where I got my sources, possibly internet experts, some of my friends, my mother, other women I’ve met briefly.
I am a recluse practically, and we’ve been meeting just the two of us so there would be no toxic environment or anything. The one with stakes to lose is me, since we work in a similar industry (well atm I’m on retail but hopefully I can find a job doing what I like again) and word spreads fast. I already have two embarrassing experiences with people who are in the industry and it does NOT look helpful at all when applying for jobs. I’m always wondering if any of those guys is ever reviewing applications and if that has any impact on it.
But what you say is true though. I hate this so much