Everyone has dating war stories, and we asked for yours: bad first dates, good breakups, online exploits, and one-night stands. Much to our surprise, that’s exactly what we got. There was the cougar who said dating in Chicago was like being a kid in a candy store, the guy who offered a look at the same-sex habits of postal workers, and one with the memorable first line, “If I had to measure it, I’d say it was approximately a pint worth of shit.” And those are the ones that didn’t make the cut. The stories here include a bar hookup that ended with endless repetition, a woman who quit weed to find love, and a man who says he’s doing his part for the war by keeping soldiers’ wives happy. Talk about a war story . . . —Julia Thiel
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Sofia Penelope Brown—555-Weed “I have no job and just got out of jail. You really think I’m marriage material?”
“Dear Elsa: A letter to first loves, cigarettes, and Chicago,” by Rose Tully
How not to hook up: Tales from the Continental’s den of 4 AM iniquity
“How do you like them Apples to Apples: A dating event devoted to geek love,” by Julia Borcherts
Defining the #perfectcompanion, some of our favorite response to our @Chicago_Reader entreaty: Tweet what makes your ideal mate
Let us indulge your inner stalker: The Reader responds to some of our favorite, creepiest, most stalker-ish I Saw Yous
