Relationship? Advice

I'm in my mid-twenties, and I've only had a couple of serious relationships. Part of the problem is that I don't really know how to flirt and I can't always tell if someone is flirting with me. I know that sounds like an "awkward teenager" problem from a cliche TV show, but that's how it is. Anyway, I've been single for a long time, and I wouldn't mind dating again, but I don't go many places where I interact with "eligible bachelors," if you know what I mean. There's this one guy, though, who goes to my church. We've talked some and we are friends. He's a lot older than me (over 12 years), but I've never heard him talk about a significant other. He's always really nice to me, but I think he might be like that with everybody. I don't know if he is even looking to date anyone right now. I tried very subtly getting some perspective from a mutual friend of ours, but that didn't get me anywhere. It's not like I would be totally devastated if nothing came of the relationship, but there is a part of me that really wants to give it a try. How do I approach this without making things super awkward if it turns out he isn't interested? Is there a loaded question I could ask or a hint I could give? Is there a way to flirt with him and know if he recognizes it as flirting? Should I just forget the whole thing and keep him as a friend? Am I in the "friend zone," or does he even know that I want something more?

People are complicated. Communication is complex. Social norms are a tangled mess.