Is there a specific subreddit (or anywhere) where I can get advice on how to help/support my friend?

I'm 23 and female, and he is 34, gay, and comes from a super-conservative state (lives in a much better larger city now). We met at Pride fest, and we also work at the same company, and have become very close friends and talk basically 24/7 when we have time.The thing is, because of the age difference and because I've never had a very close friend who is gay, I don't always know how to help or what to do to support him. He knows support him 100% no matter what. He struggles with depression, but is in every way super social and has great family/friend relationships. I'm just worried that he is really lonely, and because of his upbringing he isn't really comfortable at all with being gay even now. He's hooked up with a few guys over the years, but has only ever "had sex" with one person ever, which was a boyfriend that he had years ago. I don't really know a lot about how gay dating works, or dating in your 30s in general, but I know he really deeply wants to get married/have children at some point in his life. If I sound super young and naive describing this, it's really because I am. I just want to help him any way I can, and I have no idea how.I've learned a lot about the community on here and want to learn as much as I can. Any advice/assistance/direction/criticism/anything is greatly appreciated. :)