37 and still confused but met a guy...

Hello ECer's. I'll try to keep this as simple as possible.

I'm 37 years old and still not totally sure about my sexuality. I've never really been interested in women. I've dated a few women but generally only under pressure from other people. Those dates felt like drudgery and didn't lead to anything. I've never been in a relationship or done anything sexual with anyone. However, all my adult life I've had romantic feelings about men. I consider them romantic because I can listen to a love song and say "that's exactly how I feel about so-and-so except for the parts about kissing or sex." These feelings stop short of sexuality. I've never had a desire to have sex with a man. To confuse things further the men that I find appealing are usually older (40s-60s) and geeky looking. Because my feelings weren't typical for gay men, I never really considered myself gay. I studied asexuality, but somehow couldn't embrace it as an identity. Last year I read the book "Denial: My 25 Years Without A Soul" by Jonathan Rauch and it really opened my eyes. It showed how someone could be unaware of sexuality well into adulthood and I could relate to a lot of his experience. The takeaway was that I needed to be more honest with myself about my feelings. I decided it was time to find a man I like and date him. But how would I find one? I didn't like what I saw on dating sites and I did not want to go to a club or bar.

Anyway last month out of nowhere at a group event I usually go to this guy shows up and he seems kind of nice. A few minutes into the conversation he just comes right out and says he's gay. The conversation continues I find out he's going to another group the next week that I've been interested in for a while. I ask if I can come along. he says yes and gives me the info. The next week at the other place I see him again, more great conversation and I meet some of his friends. He's surrounded with great people who have known him a long time. He has great career achievements and is just so kind and nice and not bad to look at either. Exactly what I've been looking for. He's 40-something-ish but I'm not sure of his age. As far as I can tell he's single.

So anyway, I'm expecting to see him again in about a week. I want to approach him and tell him how I feel. I want to ask him out for dinner or maybe coffee so we can have some deeper conversation and see what potential there is for us. I also want him to understand my inexperience and confusion.

What's the best way to broach the topic with out giving too much detail or making him uncomfortable. Thanks in advance for your advice on this. I am a total n00b at this stuff.

 

Well, my guy didn't even show up when I expected him. I actually think I know where he was but that's another story. It looks like I won't have another chance to see him until the middle of April.

This is how it always is for me, whenever I like someone for any reason it takes me so long to get to a point where I actually get their contact info and feel comfortable just e-mailing or calling. So to maintain contact I depend on seeing them at meetups, religious services, classes, etc.... This is getting really frustrating, I don't know how many potential relationships/friendships I've lost because the person never showed up again at the place where I met them. :bang:

 

Well, I know if I want to see someone again, I need to say something along the lines of "I'd like to see you again. When/where would be a good time?" It's been amazingly hard to get that thru my head though.

Already have and read his posts almost daily. But I do think actually contacting him that way would be creepy at this point.

 

Thanks for the advice.
I actually have a new and better plan. There's something coming up this weekend where there's a possibility my guy could show up. However, there is a much greater possibility (almost certainty) that people who know him will be there. I could just simply ask one of them "Hey, I haven't seen x in a while, what's he been up to?" From there I could find out where to meet him or maybe even have someone relay the message to him that I'd like to talk. Some of these people are LBGT, they'll know the deal.

 

Well, I went to the thing this weekend and as expected he wasn't there. I tried my plan of asking other people about him (I hadn't seen all of your responses at that point). I brought up his name in a conversation with someone and she hadn't even heard of him. I didn't really find an opening to bring him up with anyone else, so I dropped the issue and made absolutely no progress.
I accept the unanimous assessment here that trying to reach him thru a third party is a bad idea. I guess I've been trying to think of a way to reach him that would feel "natural" to me and hopefully to him. But the fact is I haven't seem him in 5 weeks and have been obsessing about him all the while. NOTHING is going to seem natural at this point. I'm not happy with either of my remaining options, try reaching him thru social media or wait for him to come back to this place I've been going (which I like so I'd be going there anyway). In the interest of privacy I can't give you more info about where I've been meeting him, but I think if I could you'd agree that the chance of him showing up again eventually is fairly good, but not a guarantee.
Anyway, I think on a deeper level what's holding me back is two types of fear. The usual fear of failure, but also fear of success. Think about it, success would mean entering into a relationship where I would have to face sexual issues that I've been repressing since I was 12. Success would also mean being outed to just about everyone I know. My social life is a small world, and once one person finds out we're dating it would spread quickly. There's only two degrees of separation between my guy and some people I know very well who are not going to be happy with me if they find out that I'm gay. I know I need to face both of the above and the sooner the better, but that doesn't make it any less scary.
I feel like Neo near the beginning of The Matrix. I still have the opportunity to take the "Blue Pill". I could not contact this guy and never speak of him again and I'd be able to return to my safe but false asexual life. Or I can take the "Red Pill" and explore the reality of my sexuality with all the risk and reward that entails.
I think I know which path to take, the question is can I bring myself to do it?