What is the proper way to handle this one?

There is this guy I've been friends with for about 6 months. I met him playing darts (he was on a different team) and for summer season and now this season we play on the same dart team. We're friends, but people around us often think we're boyfriend/girlfriend because we flirt and hug and stuff.

However, I am open to anything with him. He's a nice enough guy and I like him enough that if he asked me out, I'd go. I'm not so attracted to him that I'm pushing that agenda, but I wouldn't mind it.

But here's the stink of it - he had a fling with my married best friend a few months ago. She was straight forward with him letting him know she was separated, but just wanted a fling. And then he got too clingy with her and she blew him off. Now she's back with her husband and is focused on trying to repair that relationship.

Wait, there's more, so my best friend, her hub and some other couple friends are all going to a festival thing tomorrow and invited me. I wanted to ask my friend to go to. My best friend is good with that, she actually thinks we'd make a cute couple, but ... am I setting myself up for drama?

Thoughts? Opinions?