Sometimes you just gotta try to read the person your best, be friendly, and flirt. Make a compliment, just try to keep it respectful, and give it some time to set in with the other person. Just don't lead in with 'hey sugar tits, you looking fine today baby gurl' or something along those lines lol. Also don't lay it on too thick, maybe just a comment in passing, like nice outfit, looks amazing, love the pop of color or something, or wow, you are really good at xyz, how long have you been into that?

I can relate to the struggle, but sometimes you just gotta take a big gulp and try to be confident in yourself (just enough) to take that chance.