Establish yourself as a semi-regular, one she's happy to see.
This means stopping in roughly twice a week and behaving yourself. If she greets you with a familiar smile and starts to recognize your drink, proceed to Step 2.
Sit at the bar while business is slow and make pleasant small talk.
Before you hit on the bartender, you want to make sure she's as sexy on the inside as she is on the out. Stop by early in the week and early in the evening, before the rush. If she's not busy, she'll almost certainly talk to you if she's interested.
Tip her well--but not too well.
Sexy bartenders are funny creatures that way. Of course, if you leave her a bad tip she'll know you're stingy and won't be interested. But if she feels you're trying to buy her affection, you'll never get anywhere outside the bar. You've established yourself as a customer, and a creepy one at that. Leave a generous tip, but not a ridiculous one.
Ask her out while you're sober, before you've finished your first drink.
Even if you've been planning to ask her out for weeks, if it slips out while you're drunk she'll think you're just, well, drunk.
Know when to hold 'em, know when to fold 'em and know when to walk away.
If you've taken the time to get to know her and she rejects your proposal for a date, let the matter be. You aren't a dupe; after all, it is the job of sexy bartenders to be friendly, and that can be easily misinterpreted by even the most lady-savvy man.
- Though bartenders tolerate ornery regulars who anchor down their favorite bar stool five days a week, she would never think of dating one. Coming in every day after you finish work and staring at her will not be interpreted as romantic behavior.
- If you attempt to talk to the hot bartender while it's very slow and she doesn't seem to be interested, abandon ship. She's not interested.
- Never try to monopolize a bartender's attention while she is busy. Remember, helping other customers is how she makes money. She'll think you're inconsiderate, or at least too stupid to notice she's busy.
- Never get very drunk at a bar where you plan to hit on the hot bartender. If she has to cut you off or kick you out, you'll just be another thing she has to deal with. Also, it makes a bad impression.