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Needless to say, if you’re a gay man looking for a hookup, Little Jim’s is for you. I think he was so hard up, that he would’ve gone home with me that night if I had so graciously offered. Of course, I speak from personal experience having to listen to an intoxicated 40-year-old man tell me how lonely he was. The place tends to make you feel a little claustrophobic at peak hours, especially when loud drunk men get in your face or back you into a corner to share their life stories. The downside to Little Jim’s, aside from gossiping bartenders, is its small size.
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Little Jim’s is cash only, doesn’t serve food, and has a late-night license so is open until 4am during the week, 5am on Saturdays, and opening noon daily. Some advice that I have been given by Little Jim’s regulars is to make friends with the bartenders who’ll hook you up with drinks make enemies with them and they’ll talk about you behind your back to everyone in the bar. Speaking of which, the daily specials at Little Jim’s can’t be beat, especially with well drinks and domestic beer for $2.25 on Mondays and $6 Miller Lite pitchers on Fridays. I personally never witnessed this but have over heard friends reminiscing about it over Little Jim’s cheap drinks. A few years ago the bar used to play videos of men going at it but, for unknown reasons, the videos mysteriously disappeared.
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The bar offers two pinball machines, a jukebox and two televisions playing various TV shows. If sex is the furthest thing from you mind, you’re likely part of the minority at Jim’s but there’s plenty to keep you distracted. Even though the bar is meant for men, actually reminding me of your grandpa’s rec room, the occasional woman can be seen at Little Jim’s, most likely dragged there by friends just like me. Before making my fist trip about a year ago, I had heard some less-than-pleasant things about it, such as the bar’s nickname “pig farm” (named after the men or “pigs” that want to use other men for sex) and its notoriety as the sleaziest bar in Boystown, which kept me from high-tailing it over for a drink previously. And it’s only because one of my lonely-I mean lovely-gay male friends wanted to go there. I can honestly say that the only times I have ever stepped foot in Little Jim’s were after a night of carousing at other Boystown bars like Hydrate. Little Jim’s is meant for getting together with friends, having a few drinks, chatting and, to be blunt, an easy place to meet easy older guys and “bears.” Don’t blink or you’ll miss it-it’s a tiny late-night hook-up joint disguised as a neighborhood bar. For those of you history buffs, Little Jim’s Tavern at the northeast corner of Halsted & Cornelia, was Chicago’s first LGBTQ+ friendly bar to open in Boystown back in 1975.