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

  • t�mEnglish
    3·
    3 months ago

    You could ask:

    1. What’s your best quality?
    2. What’s your worst quality?
    3. What does “home” mean to you?
    4. What’s your favorite childhood memory?
    5. Who are your role models?
    6. What is your relationship with your like?
    7. What is your idea of happiness?
    8. Where do you see yourself five years from now?
    9. What goal are you working toward right now?
    10. What’s the biggest challenge you’re facing right now?
    11. What does retirement look like to you?
    12. What’s a skill or quality you would like to develop in yourself?
    13. Have you ever experienced a life-altering moment that changed your perspective?
    14. What do you consider your biggest accomplishment so far?
    15. What’s the most difficult thing you’ve ever been through?
    16. How do you cope when you’re upset or stressed out?
    17. What are you grateful for?
    18. What’s the best piece of advice you’ve ever received?
    19. What’s your worst habit?
    20. If you could change one thing about yourself, what would it be?

    Also is kinda tricky; on one hand you could try to find out what hobbies he likes and do them together somehow. But if you do too forceful it might be too much…

    So what have you done so far?

    • Mothra@mander.xyzOP
      2·
      3 months ago

      We’ve been hanging out a few times, but it wasn’t “a date” even though it was just the two of us most times. We don’t see or talk as frequently as people who are about to start dating do though. I was hoping to build some momentum but from the replies here I’m getting the idea that I’m going to have to man up and ask him on a date formally.

      • t�mEnglish
        2·
        3 months ago

        That exactly what you’re going to have to do it seems.