Also like, longer version: I know the rejection can sting, but I've never met an adult who reacts meanly to "Hey, this conversation is going well, I wanna get flirty but don't want to make you uncomfortable. If I see a good opening, mind if I flirt?" or something like that.
You might get told no, but as long as you just accept that no with grace and go "Okay, well, conversation is still fun if that's all right." You might get told no, and the conversation ends there because they would rather not continue afterwards. That can sting, but honestly if that happens there was a good chance they were looking to end the conversation regardless so you just saved both of you some time.
But if a whole-ass adult gets nasty with you or mocks you for asking? Then good news! You've learned you dodged a bullet because regardless of what else they are, they're the kind of person who mocks consent checks and you really, really don't want to be involved with someone who thinks that's worth mocking. Best case scenario? They're immature or haven't properly unpacked some things, which would make them...less than ideal to be with.
Let's not go past that best case.
And hey, you might get told yes. From personal experience, I'm more receptive to flirting from someone I am vibing with but not sure about if they ask first, and I know i'm not alone there.
And also? Because you asked, they won't go "Wait, was that person flirting with me?" You've established that comfortably and in a way that - if nothing else - establishes you're the kind of person who respects the wishes of others and that's a damn attractive trait.
