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A bartender can be the best and most subtle wingman there is — especially if it’s a slow night.
It’s easy for them to get information about someone you’ve been eying, strike up a conversation that somehow gets you involved, and, (if they’re especially nice) ply a couple with some free drinks to help keep things going.
(I’ve totally been sent drinks from the bartender when out on a date because it looked like we were “having a nice time.”) If you sit at a bar by yourself and basically STARE at a cute guy or girl, you will seem like a predator.
Bars are crazy on weekends — bartenders are swamped, people are out with big groups of friends, the music is loud, and it’s probably less weird to stay in on a Saturday night than it is to go to a crowded bar, alone. Girls don’t want to be approached on a Saturday night by the guy who is there alone.) On a weeknight, however (especially Mondays and Tuesdays), bars are much more relaxed places, full of regulars enjoying a relaxed drink or two.
Bartenders are much less frantic (and much more willing to pour you a free drink or two), and patrons much more likely to engage the people around them.