If you look anything like your avatar, you might want to put on some weight and lose the swords first J/K, brutha.....I say GO 4 IT !!
I dated a bartender or two years ago. remember, they are constantly being hit on. I found out that if you're a regular, just chat them up for a while first. Be patient. Chances are she may even drop a not so subtle hint when the time is right...as long as you don't look like that avatar.
Hitting on the bartender ....WHAT!...I would never hit a lady..