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

2 points

Your and his age are gonna be major variables here. Conversations and relationships work very differently at different life stages.

You sound like you’re maybe a teenager? Try asking interesting questions that require some thought to answer, but still leave room for your friend to give an easy thoughtless answer if they want to. Where do you think we’ll be in X years? What’s something you thought you wanted but as you’ve gotten okay have realised you actually don’t? What do you think we do now thar future generations will think is crazy? Listen to his answers and ask followup questions.

Personally, I’ve always been most impressed by directness, honesty, intelligence and courage.

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4 points

36F 30M, both neurodivergents if that also plays a role. Neither particularly lucky in love, though finding people to date isn’t hard for either. Both in many ways immature so I don’t take personally you presuming I’m a teenager. I absolutely feel as dumb as one to the point of asking this question. Thanks for the answer.

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8 points

Neurodivergent romances are awkward as fuck. Dunno what to say except sympathy.

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5 points

relatable

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2 points

After 30 you should both be able to handle rejection and reject in a nice way. Just make sure you are both sober and sprinkle lots of compliments.

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3 points

It’s not me downvoting you btw. Maybe you are right, perhaps I’m not mentally prepared to handle it. At least I know what to talk about next time I see my therapist

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74 points

Okay, fifty year old asshole here. I’ve danced the dance more than a few times.

Don’t waste time fucking around. You have the feeling, you be up front, honest, and let whatever happens happen.

A real friend? Trying to go romantic and failing won’t change a thing long term. A real friendship is too deep to destroy by just not working romantically. And if it isn’t that deep a friendship? Then something would have ended it eventually.

Now, if things don’t work, but only one of you thinks that, it can take time and work to move past, but it will if the friendship was real in the first place because you’ll value each other more than the failure can break.

You also have to be prepared to hear a no, and then learn to move past the no. If you can’t, then chances are it wasn’t that good a friendship to begin with.

There’s going to be nerves, but you just open up, let it go, and let the other person respond. Don’t do any big gestures, no movie crap. Just be the person you are and talk about it.

Me? Once I got past the whole fear of rejection thing, it was always easy to just say “hey, we’re pretty close, and I’m feeling some extra love here, beyond the friendship part of things. It seems that’s reciprocated, so how about we try this? Let’s do a formal date and see if that gives us a jumping off point.”

The conversation goes from there to whatever the next thing is. Sometimes it’s a no, and solutions it’s a yes and things don’t work. But sometimes it’s a yes, and things do work.

Right now, me and my wife (that started as friends, and didn’t even realize we were moving into romance until I told her I loved her and things moved kinda on their own) have occasional dinners with three of my exes that are still good friends. And I’m still in contact with others that aren’t close enough location wise to have many visits.

Tbh, the only exes that I’m either not still friends with, or wouldn’t be if we were in the same location, were ones that didn’t start as friends.

Seriously, the next time y’all are going to be together, when there’s a moment that the feeling it’s going somewhere, say something.

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11 points

Thank you

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3 points

This is a good one. Maybe there isn’t a way? Maybe it’s not the right time?

My wife and I are two people with different interests who just happen like each other and have a family together-we often comment on how if we had met any earlier in our lives we would definitely not like each other.

For the most part of our marriage I worked alot. But we were always together when we could be.

Currently this is the most we have been together (last 6yrs of 25) because we now work together in our own place, and the kids have grown and moved out…and we still like each other!

Love is not a question if you like each other, and you can be two people who are together. You don’t have to have deep meaningful conversations to make a good relationship, my partner is a empathetic, thoughtful and philosophical person and I tend to go for the fart jokes.

But we get each other. Do you guys get each other then you are together?

Hopefully this rambling statement makes sense, from a different perspective. I’m tired and am having my first cup of coffee.

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3 points

Would you say what you’re seeking is “more intimacy,” up to, potentially, the most possible intimacy?

I would suggest looking at his different interests and getting curious. If you’re interested in the guy, it should be pretty easy to find reasons why this film or that game are endearingly-this-or-that in a way that makes you like and respect him even more.

Then, you bond over it; by trusting his taste (intimacy) enough to check out that show or whatever interest, you now have an opportunity to get deep (intimacy) into what you each individually felt (intimacy) about it, and maybe you felt something in common. That’s some foundation for intimacy.

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7 points

Ask him open ended questions about what he likes or finds interesting. Ask him about times when he was afraid for his life or the most memorable vacation he’s been on. Ask him about his goals or aspirations, embarrassing or funny stories, where he’d most like to travel, etc. Conversation flows more naturally when people are talking about something they’re excited about and you might learn more about him when he describes his past or feelings or wishes. You can use the info you learn to ask follow-up questions. Just make sure to actively listen and let him talk. Don’t just be thinking of what you want to say next. Maybe he’s afraid to open up to you or look dumb. Show him that you can be vulnerable and share a funny embarrassing thing that happened to you.

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