Thanks for trying though TS! I know, I really don't want to be presumptuous. But I also have resolved with myself (and speaking to a few others) that if no obvious moment offers itself (e.g. him offering to pay or something of that sort) I will end the night by a very casual "tons of fun but hoping to be friends" thing. Like an adult.
But I feel like such a teenager. As a drinker I'd just be like, Oh well, a few awkward hours, he'll either get the picture or he won't. Now I actually have some of my awareness back and don't want to be a jerk. But that's not really something I've practiced!