Jaguar, I'm a long time go-out-aloner too. I'll tell you this -- when you're by yourself, *some* people do attach a certain stigma to that: he/she must be desperate, a freak, etc.
The key is to hang out where peeps don't think that way, and that means locals rather than people from the hinterlands who may just drive into town once in a while for a show and then leave immediately afterward.
Your best bets are non-theme bars with a certain regular contingent. Hang out more than a couple of times at a good bar and people will start to remember you. Weeknights are better than weekends because a smaller crowd means less insularity. Chit chat with the bartender. Smile at people. Offer a light. The Velvet Lounge bar is good for this, Polly's, Townhouse Tavern, Fox & Hounds. Sometimes too, the downstairs bar at the 9:30, on the right night.