Lol you guys are too funny....
I believe you will struggle socializing in bars anywhere... the better alternative might be to join one of the gay sports leagues or to go to a bar during the week when they are having trivia, karaoke, etc. Just google for direction, dates.
If you want a map of what is going on the bars, to the extent of my knowledge:
Sidetrack - everyone makes at least one stop here during the night. Affordable drinks, lots of places to walk around, good looking people. Hard to strike conversation with strangers, since they are in groups.
Progress - the new sidetrack/ minibar. Not sure if it is the music or the lights, but good looking people are crowding here. Also hard to strike conversation, mostly groups.
Replay - assortment of craft beers, free video games, no cover and a porch. What could be better? If you go by yourself you can always enjoy Street Fighter with a beer :-)
Hydrate - small, with cover, you have to be into that music. Maybe good for dancing at 2 am. Shirtless is appreciated.
Closet - Lesbian bar that turns gay after 2am. Everyone is already drunk and friendly, good to start conversation. Not much else to do, small. Know your drink or the bartender will be angry at you. Ask about their famous bouncer who became a tv personality.
Roscoe - younger crowd and their admirers. It's fun if you like throwing paper napkins to the air while Rhianna is singing about finding love in hopeless places.
Scarlet - small and dj with unique point of view, but can be fun. If you are inside you are dancing, no escape. Go there alone and in a good mood and you are going to make a friend. Laid back crowd.
Wangs - do not go there on the last Friday of the month!!! lol
Minibar - it can be alright, they are known for attracting pretty people and nice lights and sounds.... you be the judge. Best part is the stripper pole downstairs, everyone must spin around it at least once in their lives.
Spin - pool table, drag queens
Circuit - latin
Bonsai - I have no idea what is going on there.
Charlies - they have gay country dancing, and after two is a hangout for those not looking to go home alone. They do have smoke machines in the dance floor and restroom that invites interaction.
Cellblock - seedy place with friendly bartender. Could be interesting, but from my experience it is mostly empty except if there is a rubber/ leather event going on. Stop by to peek at the dark side of life lol
Little Jim - mostly for seasoned gentlemen, interesting seating arrangements. If you come here strike a conversation with the bartender about the bar's past and learn a bit of chicago history
North End - very laid back. Come here for the darts, punch machine, pool table and friendly bartenders.
Lucky Horseshoe - they have strippers and their admirers.
Berlin - not officially gay, but it is the intersection of everything. Can be the best night of your life or the worst. If you are into Madonna, this club becomes a temple every last sunday of the month for all her followers. Might be worth a visit, it is like going to her show but for $5.
Big chicks - great place to go by yourself if you have an open mind. Laid back crowd. Dance floor is empty until 12am, when they serve free shots and people start dancing. Worth checking out :-)
Marys Attic - interesting place, dance floor, chair lounge and leg lamp.
Touche - for seasoned gentlemen into leather and other fetishes.
Jackhammer - also for people into fetishes, but with more room to walk around. The sex shop next door is connected, feel free to browse their inventory while having a beverage. When you are in the main bar having a drink and watching porn, remember that the restroom is to the right. Be careful when you go to the left and downstairs! lol
Baton - drag queens
Downtown - regular bar, I guess for the people that live there?
Second story - ?
Pilsen/ South side
Hope this helps. Go out exploring and come up with your own opinions, it is a good excuse to be out :-)