We asked our listeners their thoughts on hitting on servers.  Here are some of the responses:

You can’t ask for their number, you have to give them yours. Leave it in the black check presenter with your tip so there’s no pressure. That way, they are in control of how to proceed, don’t feel obligated to engage just to get their tip, and nothing is awkward.
– Kari

Become a regular! Without being pushy or inappropriate ask a question or 2 with each visit to get to know them and open up. Asking for or giving your number the first time you sit in their section is creepy. Leaving a big tip wouldn’t get my attention at all… Knowing that you enjoy my company would.
– Karen

You don’t! It’s already creepy and if things don’t go as planned you have to go somewhere else. Plus nobody wants to be flirted with at work especially if they aren’t looking great.
– Jenneh

Be genuine!! We can always tell. Also, don’t have your people around talking about it. That’s just weird for everyone.
– Beth

The customer is in a power position. It’s not fair to the server. And please don’t mistake my friendliness for flirting I have to be nice to you. It’s for my job
– Dill Dilly

Why not try to pick up someone who’s job isn’t to smile at you and treat you well.
– Brigitte

Usually being courteous and light hearted flirting can get you started in a good way. After that it’s a 50/50 shot. I’ve been shot down by 5 of the 8 bartenders I went after, but they were all in committed relationships, made a bunch of friends and I always got a slightly stronger drink when I asked for it afterwards.
– Tony

You just don’t.
– Kimberly

Two hands; lift with your legs; not your back.
– Michael