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.

I already responded somewhere else, but I have more response that doesn’t make sense in that context.

First, about deepening conversation. I don’t know about this guy, so I’ll talk about myself. I have things I’m interested in, let’s call them “interests”, and I like to talk about them. And the only thing that stops me from talking about them constantly to everyone is the social understanding that they don’t want to hear about my interests.

So all it takes to have me talk about stuff is enough questions to demonstrate you really want to know.

“What do you like about blah blah blah?” will probably get a short answer because he’s used to people not really wanting to know more, so he’s giving the smallest answer that answers the question. But then, you ask a question about his answer. “Huh, how is that different than blah blah?”

Now maybe longer answer, you listen and ask based on that, and if you can manage it you could also circle back to a previous answer to connect some dots. That’s now a discussion! Now, of course, you do have to listen. Unsure if that’s a skill of yours or not.

As for the asking out, I think you should do it. But if you don’t trust yourself to deliver the speech live, you could write it down / print it out. Just make sure it contains escape hatches for him that assure him it’s okay if he doesn’t share your feelings, and that he can just tell you if that’s the case, and probably ends by saying he doesn’t need to necessarily give you an answer now and you’re just happy you could get it off your chest. I think going for something casual is better than something heartfelt and romantic, but I don’t know the two of you. The most important thing is that he knows, and the second most important thing is that you don’t want it to wreck things if feelings aren’t mutual.

And if you don’t want to awkwardly read it, you could just hand it to him and let him read it at his own pace. This lets you watch his face while reading, if he makes facial expressions and if you can read them.

I would recommend against an email or a text, though. It feels like, from the bits of your personality I’ve picked up here, the time between when you send it to whenever he responds is going to be absolute torture for you. Whereas he might just be busy and not have even seen it yet, you’ll already be inventing bad scenarios and deciding which new city you should move to since you obviously can’t stay here, etc, etc 😉

So probably best to deliver it in person, maybe at the end of a hangout, so you can be sure he received it and read it. And I know you may be scared, but don’t tell him to read it after you’re gone, because that’s now email territory where you can’t ever know if he’s read it yet! Just have him read it, assure him it’s okay if he doesn’t agree, and let him respond. And even if he doesn’t have an answer now, you know it’s done.

Good luck!

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.

To echo what a lot of people are saying, just go for it with confidence (which is easier said than done, I know.) “Hey, I think we would be a good couple and I was wondering if you wanted to go out sometimes.” And if they no with same confidence (or fake it) “I’m so sorry, i must have misread the situation. Don’t worry, you don’t have have to be awkward around me.”. And that’ll take the pressure off of both of you so it’s not weird

You could show him this post. Communication often comes down to just being straight forward with your message and allowing people to respond rather than imagining it.

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.

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?