I agree with pps above saying that this is about the power balance, and also I think the setting itself is important.
For example: if I was at work and men kept making comments and compliments about my appearance, I’d be uncomfortable- I’m at work. I’m in professional mode. It’s not appropriate to do so beyond the sort of ‘oh you got your hair cut, looks good, right about this dataset..’ thing.
If I’m at some fancy ball thing and dolled up to the nines, and men compliment me on my appearance, I’m Ok with that (and ok with women too.) if they pester then again I’m back to not being OK with it, because it’s gone beyond what’s appropriate in the situation.
There are settings where flirting is acceptable and ones where it isn’t. A street march, carnival, party, night out etc is the former.
As long as all these interactions were light hearted, and he didn’t feel threatened, then I think it’s all OK. I’m glad he had fun - pride generally is usually a really nice atmosphere.