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

  • Pumpkin EscobarEnglish
    31•17 days ago

    Shoot your shot, player.

    Don’t go crazy or over the top, don’t overdo it, but just say it. If they’re a good friend they won’t be scared away. If they’re like you that way you’ll both be happier.

    Don’t overthink it, ask them if they’d ever like to hang out or do something more like a date.

    Ballsy, direct, badass. That can be you.

    Dating is awkward but life gets a lot better once you get more comfortable with it. Everyone is a dating idiot until they’re not, there’s a good chance your friend is still in the idiot stage and maybe hell be over the moon that you helped push through it.