I do not know how either maybe Kaiser can answer this thread and give us advice she a real player. I would say start by saying hello and observation.
I have always been flirty with girls, but am starting to be flirty with guys. And trust me, even with severe social anxiety you can manage to flirt with people. @golgari - you have such a nice smile. you always look so happy. There, I flirted with you. That's about what I would say to maybe a waiter I like. One or two lines indicating interest in another person. Keep it light, simple, short. Practice it if you get nervous in front of the person. I had one situation, a really short, cute redheaded gal that was a server at a restaurant. We would go there twice a week, just so I could see her. Anytime I saw her, I'd put on a happy face, and give her a compliment. She finally got to the point, she gave me her number. On the bottom of a shake cup, so I never saw it. A day or two after that I was driving her home after work. She left town shortly after, but the steady indication of interest actually worked. And don't try to be subtle about it. Let them know you are flirting. You have a nice smile, eyes, face, butt... Smiling, eye contact. Hope that helps. You just have to reach down and find the courage to put yourself out there a bit.
