Flagpole, sounds like you were mostly playing in dives and honky tonks. I'm imagining Harleys in the parking lot, chained wallets and a mechanical bull. What do you expect to find at places like this other than skanks and pathetic scenes at 2 a.m.?
Talking to random people at a bar isn't my idea of a good time. I get it that some people like that though. I DO like occasionally playing music in bars, but that's it.
There are many high end clubs and bars in most cities where classy, hot women of all ages hang out. I'm not saying that going solo is ideal, but in the right places you can go by yourself, mingle and meet cool people and not look like a creepy dude with no friends. If you're friendly and upbeat and don't sit in a corner acting like a weird loner, you can have a great time. If someone asks why you're alone just say, "My buddies couldn't come and I wanted to get out of the house". Totally true. I've gotten numbers and scored a few times. On one occasion a woman 12 years younger than me - a divorced pharmaceutical rep - took me to her very nice home in her Lexus. Another time, it was hot blonde dental hygienist 15 years younger who was a total freak (out of town on business, we went back to my hotel).
Like another poster said, when I separated from my ex after 20 years of marriage, I didn't have any local single friends. All my friends were married and not into the bar scene, except for a few work buddies in different cities miles away. Plus, sometimes you lose a lot of friends in a divorce. I wanted to get out and have fun after years of being "family man". So I started hitting some of the nicer, more popular clubs in town. Had a great time and got lucky a few times.
Bottom line: It's better and more fun to go with a friend or group, but if you're fit, attractive and have a good personality, going it alone can be done successfully.