How to read the "signs" with a shy/awkward guy

My crush is roughly 10-15ish years older than me (but I'm old enough where it isn't automatically creepy if he's into me), I get the impression he's a little socially awkward and on the shy side, he's had his moments of going way out of his way to be really sweet and friendly to me but other times he acts a little...either nervous/shy or just standoffish, depending on whether I have my rose colored glasses on.

He always talks back to me and carries on the conversation, so that's nice. I never feel rejected by him, it's just hard to tell if there's a chance he's interested. I brought up the age gap because he's also mentioned that in passing and I was wondering if he might be afraid of coming across as creepy if he showed interest. This is also why I don't want to straightforwardly confess, because I could be putting him in an uncomfortable position if he thinks of me as too young for him.

Are there any more subtle ways I could find out if I have a chance? We get along really well and have fun conversations, he's also one of the nicest people I've ever met and again, there have been several times where he went out of his way to do really kind things for me without my asking. I could honestly see it going either way with him; he could like me and just be nervous and awkward about it, or he could just be a genuinely nice guy and I'm reading into things.