New to dating guys. How do I move forward?

I'm 28 and I've known I'm gay my entire life but pretended to be straight. I recently came out to some best friends and it went so well! My Dad was totally supportive but mom had a total breakdown.

Some context, I'm the kind of guy who needs permission for everything.I don't want to be told what to do but I need them to say "it's okay". I wish I wasn't this way but I've always been nervous of intimacy but thought it was because I was dating women and I was gay. I've never been good at starting things or making the first move so it turns out that I'm still that way even with guys.

So this is the second guy I've started seeing. It started on a dating app and he said he's looking for a jerking buddy. As time has gone on for me, I have changed how I approach these situations and always say "I'm not into hookups" But he asked what I was looking for and I said "I just want to hang out, talk, laugh, get to know you and see where things go!" He was super into that and admitted that he doesn't really like hookups either. I'm not a bad looking guy and he was totally my type so after not that much talking, we settled on having a beer beer on the porch at my place in a few days and that went so well! We really hit it off and both of us agreed that we wanted to hang out again. He didn't take me as the kind of guy who was just looking for a jerking buddy so I promptly forgot about that to be honest. He's a bit timid, a little shy at first, over all just a SUPER nice and kind guy! We kept hanging out a bunch, date nights, texting all the time but every time we would hang out it was just that. Hanging out and talking, watching some show on netflix but nothing physical. I knew he wanted more because we were clearly into each other but I can't make the move. So I said the same thing to him that I said to the first guy I had seen. I'm not really a first move kind of guy. He said It's not too late to learn and wanted me to make the move! This stresses me out! Even though that's the permission I desire, I was still all locked up. Eventually after many many dates I worked up the courage to kiss him but it was only because I poked at it in a conversation earlier that day, again giving me confirmation. He's been so patient with me which is amazing but now we've been slowly moving forward for a while now that I'm starting to get confused.
We keep hanging out, gone to trivia, met his sister and her husband, going on a hike this weekend. A few weeks ago we took photos of the sunrise on a hiking trail. Hung out more times than I can count any more, date night, pizza and a movie. Things seem like they are going in a "relationship" direction but I don't know if it's just a fling or a thing? I'm pretty okay with both. I'm really starting to like this guy a lot and would love to date him but if he didn't then I can lean on, I'm new to this and experience is good!

I'm confused on so many levels though. Which is it?
If this keeps up, are we dating? Can I hold his hand in public? Do I go in for a kiss when I see him? Or does he still see me as a jerking buddy and only wants to be physical in the bedroom? Mixed messages kind of. We've had some dirty conversations so I know he wants to get more physical than just kissing and cuddling but I have NO clue how to start that because of some internal block. I do want to do that stuff so bad but can come up with every excuse to not. It's a two part issue, I don't know how to move forward in a physical way or emotional. I had forgotten about our first messages because we've had so much fun together. I'm just at a loss. I feel like a conversation with him could alleviate this but that's how I messed things up with the first guy I was seeing. It turned out in the end we both wanted the same thing weeks later after that conversation but we misread our responses to my questions about where things were going.

Thanks for hearing me out. I just don't know how to move forward.

 

I just realized this might need to go in Family, Friends, Relationships. Sorry about that!

 

Thank you for all the help and giving a good 3rd party look into this. I really need that and as comfortable as I am with my best friends, it's not somewhere I want to put them in the position of trying to give feedback on something they are supportive of but not entirely sure of the advice to give. And I am really excited! Things seem to be going well!


I wish I wasn't the one who had to initiate but I guess I'll grow from this!

Communication didn't work out with the first guy but we're still good friends and still hangout and chat which is great.


This is super embarrassing but I have this large hernia that I'm getting fixed soon but covid so who knows when. Doesn't hurt but I'm SO self conscious about it and hate it and I think it's one reason I'm having a hard time moving forward. I can hide it pretty well but can’t always and it still bums me out. I feel like I have to mention it to him at some point before we get more physical and hope he’s okay with it for now. But I guess I’m nervous because this is my first non-hookup where things might get serious and that scares me a bit. Had one hookup, some oral, hated the situation but loved the oral, couldn’t get hard, too rushed but still liked helping that guy out.


As for the relationship side, I think you guys are right. He might not have expected someone that he might date but I think we've gotten past the hookup stage, this would be a lot of work from him to be a hookup! I think it's interesting that he might be more nervous than me, he certainly was on the first date but warmed up after that. I have an odd bit of insider info that I’m trying not to lean on but the first guy I saw had a date with the guy I’m seeing now once many months ago, they didn’t hit it off at all but they talked about what they were into. He’s a little bit dom which is why I thought he would want to initiate but as you guys picked up on, it’s pretty clear I’m the one to do that (maybe that is his way of being dom a little?). If it’s because he doesn’t want to pressure me or if he’s just not into going first, it’s on me. I need to dig deep and just kind of go for it! Labeling the relationship can wait I think. I want to see how things go for a bit more and really make sure we’re both on the same page before asking if we’re official.

 

Soooo, he had a really rough day the other day with his folks. He moved back in with them to finish school and he just moved back to this city. It had been a busy week so we couldn't hang out at all but the day we planned on hanging out is the day he had an issue with his folks and their problems. He came over and he talked about some of his home life problems. I was there for him and listened and gave supportive feedback and shared some of mine without delegitimizing his which all went well! It felt like for the first time we were just talking and nothing was contrived or that I was having to "try" like in the first part of any relationship which felt awesome The best part about this conversation is that we got to talk about our upbringing and the "complexes" we have because of that. More or less danced around some of the subjects I wanted to talk about without having to deep dive into them. Turns out that he just got out of a LTR like 3 months ago and is still a little hung up by it even though that bridge was burned but it still hurts him which I totally get. This more or less means he's probably not ready to put a label on it but it was subversly said by both of us that were kinda seeing each other. I talked about how I enjoy open communication and he mentioned that's something his working on but also wants that.
I think all in all, for it being new to me and letting him recover/slowly roll into this sounds like a really great thing for both of us to be honest. I'm just going to let it all play out before asking for labels I think because I know he's still timid from his last relationship, even though he ended it.

Thanks again all for hearing me out and the help you've provided! Wish me luck!

 

Sorry to keep drilling into this. It's almost therapeutic even just to post this somewhere.
I think I'm going to have to ask him how he sees us. I feel like things have gone backwards a bit and he's pulling away. I just get this feeling I'm being friend zoned. And going back to the earlier conversation about how it all started with a "jerking buddy" well, maybe he is just looking for that. He's busy with school, works part time, living with his folks while he goes through school, he just might not be ready for a full on relationship. I'm a bit invested at this point so I really just want to have a conversation about the potential, not asking "are we dating or what?" kind of thing. I don't know unless I ask. I can hold on and be patient as like I said before, I'm a slow mover myself, but I also don't want to "waste my time" as it were. That's a terrible way to say that but if things aren't going to progress, then I'm okay with being friends but it's only fair to me to know that he's not looking to date and I more or less am.

We have trivia tonight and maybe I'll ask him if he can go on a short walk with me after and have a conversation about it. We will have had a beer or two and that'll calm my ridiculous nerves about asking this kind of question. I'm nervous because I care and I very much hope that he doesn't say he's not ready to date right now because I really do like him but I'm ready for if he's not.