Come on now, Sam. Don't feel like a fool!
This is part of life as a gay man. Hell, it's part of life for ALL people, gay or straight, male or female. It's just that us gay guys are often "undercover," so to speak. We're on the lookout for "our own kind" quite a bit -- so sometimes we get a bit too hopeful a bit too soon. It's no big deal.
Dude, you may not believe me but I was going to post here when you first asked the question and state that I thought the guy in question was probably just chatting you up. But everyone else seemed to think that there was something more to it. I decided to shut up about it and just let events take their course.
But I am ALWAYS dubious about these sorts of things. Thought I have a very optimistic outlook on life, I often tend to expect LESS and then I usually find I am happy and surprised to find out I've gotten MORE than I bargained for.
The thing is, Sam... there still remains some doubt. I am aware that his actions in front of you mimicked his actions in front of others, but... you still don't know he isn't interested, do you?
Look, I've met lots of gay dudes who are TALKERS, too. They'll chat up EVERYONE. But they also want to screw some of those guys. And some they do not. But still they will talk to anyone at all.
So you never know. I do think this situation requires a lot of finesse, though. My advice: continue to be friendly to the guy and just see where it goes. If nothing happens, so be it. If he's interested, he'll steer the conversation toward more questionable topics when the two of you are alone sometime. You can also do the same, guiding the discussion gently near subtle areas and slyly checking his reactions. A fish nibbling at the hook, if you will. You'll feel the tugging. If the tugging stops, you need to bait the hook again or try a new fishing spot: that one has escaped. If the tugging gets a little stronger, play out some line and consider when is the best opportunity to reel him in!
And finally... if I'm reading between the lines correctly... you are concerned about age, etc. Don't worry, dude. All kinds like all kinds. I get hit on by teens, twenties, thirties, forties, fifties... well, I'll stop there because anything over that is a bit too close to Daddy's age for me. Attitude and confidence FAR outweigh youth -- at least for some of us.
Good luck.
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