So I go to this bar each week for Karaoke. There is this bartender there who is about my age, cute, and he is always smiling and winking at me. We don't talk much because he is always busy taking care of people ... I always go in on busy nights. Should I read too much into that?? How could I test whether or not that's just his personality or that he might be into me?
Hmm...Is it a gay bar? I would try going at a less busy night but seeing as that's a given there must be some other issue. Bartenders are kinda forced to be "Friendly" though seeing as they live off tips. Keep that on your mind but all put aside if he's cute FIGHT to talk with him. Next time...buy a beer...leave a little tip and be like, "Hey, been noticing you've been watching me." And then make a witty joke. Even if you only get a minute....You can leave an impression. Maybe get his digits for a more quieter enviroment.
You should go for it and speak with him some more. Even if he's straight or doesn't like you in that way, at least he'll be a new friend.