After a particularly invigorating tango in one of the last classes, Brett asked me to dinner. When he walked up to the house that night, my roommates and I were on our screened-in front porch drinking mint juleps. They spotted him first—and their jaws dropped. We were used to grunge guys, and Brett had forgotten to mention that he was an actual cowboy (grew up in Montana; spent summers on a ranch), so his idea of ‘dressing up’ was a tucked-in checked shirt, huge belt buckle, cowboy boots and tight jeans. In 2008 Chicago, that’d be hot, but in 1997 Indiana, it was super embarrassing to be seen with him. We dined at an Irish pub, where my fears were confirmed: He was extra-Christian (I was going through an atheist phase), familycentric (I hated kids) and very sweet (only a bad-boy cowboy would’ve done the trick for me). I never called him back, not even after he left daisies and a sweet card on my porch. But Brett and I will always have tango.—Gretchen, Logan Square

Bump in the road
I had been talking online to a guy for a couple weeks and arranged to meet him in the lobby of my building after work before having dinner downtown. While I was dressed like I walked out of an accounting firm, he was wearing a baggy purple tank top, stonewashed cutoff jeans and Tevas. He also had a big-ass (we’re talking grapefruit-size) tumor growing out of his (bald) head, which he’d failed to warn me about. I tried not to stare too much as we walked to a food court where we went dutch. We had a painfully polite conversation over our plastic trays for 30 minutes or so, and I never saw him again. That was the last time I agreed to meet anyone without seeing a photo first.—Lara, Avondale

Bent out of shape
I had expected a casual date that wouldn’t lead to anything serious, but as coffee became dinner and then led to my place, my inner skeptic faltered: Was I really into this guy after all? It certainly seemed possible the next morning, as we texted mushy drivel back and forth while he traveled home. Still orgasm-drunk from the seriously amazing sex, I dropped my phone when he texted, “I think I hurt myself—my dick is kinda bent and has a red lump.” After I sent him a dozen “WTF?” texts and he went to the doctor, he awkwardly told me I got so tight I pushed him right out of me, and the “pop” happened when he tried to thrust back in. His doctor advised that continuing to try to have sex with me could cause injury…and—oh, by the way—he wasn’t really over his ex, anyway. So in addition to being a relationship skeptic, I now worry that my crotch is a deadly weapon. At least it was good for my friends—they love calling this douchebag “Brokedick Mountain.”—Renee, Lakeview

Fly boy
Once I was riding on the bus, and there was this really cute girl across the aisle from me. Being an artist, I thought I’d try the old “Sketchbook Mack” trick: I drew her picture as we went along and there were flirty smiles and eye contact. It worked, and I got her number. On our first and only date, however, we met for a drink, chatted a while, but then she went home despite all my charms. On the way home, I found out my fly was open the entire evening. Case closed.”—Ed, Bucktown

Child’s play
When one of the best-looking men I’ve ever seen asked me out, I was excited and nervous…really nervous…so nervous that I couldn’t stop myself from saying the most awkward, conversation-halting things. We went to a movie and coffee, and when he walked me back to my place, he looked at my outfit and said, “Hey, I’ve been meaning to tell you, I like your pants a lot.” I’m a small woman and I was wearing a pair of dark brown plaid pants I found in the children’s section of a vintage store. Nervously, I blurted out, “Thanks. They’re from the children’s section. Play your cards right and you can say you got into a 14-year-old’s pants.” Immediately realizing that the line between “things you should say out loud” and “things you should never, ever, ever say out loud” had been breached, I tried to backpedal by stammering, “Not that I think you’re into 14-year-olds…or their pants…or any teen fashion really…,” but there was no recovering. We didn’t really talk much after that.—Christina, Edgewater

Punch drunk
I’d been flirting with my editor at our college newspaper since the school year began, so we made a date at a coworker’s apartment after work one night. By the time I got there, my boss/date had consumed so much vodka she immediately sat on my lap and started kissing me. This wouldn’t have been so bad if she didn’t start throwing up an hour later. I brought her a glass of water and she promptly threw it at me—twice. By the end of the night, I was coaxing her to go home (to her girlfriend, who called her incessantly). Luckily, in my family, awful first dates signify long-term partnerships—my dad stalked my mom in college and then locked himself out of his running car on their first date, so…my drunken cheater boss is now my girlfriend of three years.—Trish, Ukrainian Village

Pet peeve
It was my first date ever with a girl. I met her at a youth group for gay teens and she called and asked if I wanted to hang out; I was nervously excited and agreed. She then asked if she could sleep over because she didn’t live too close to me. I reluctantly said okay. She then somehow convinced me the only way she could sleep over was if she brought her dog. I said no way, but somehow she persuaded my dumb ass. Her boyfriend dropped her and the dog off and I had to sneak them downstairs. She then tried to convince me to sleep in the same bed with her even though I was annoyed with this bitch the second she was dropped off. I drove her back home the next day and told her to lose my name and number. When I got home, my stepmom asked me if I had a dog in the house because my two-year-old brother kept saying, “Dog, dog.” Needless to say, I didn’t date anyone for a while afterward.—Mia, Lakeview

Dear diary
It was freshman year of college, Brit lit. I was quietly dismissed for a doctor’s appointment and the next thing I knew, he had bolted out of the door after me. We exchanged numbers and he asked me out. The next Friday, he picked me up in his SUV. The first thing I noticed was a rose dangling from the passenger window. A BEAUTIFUL ROSE FOR A BEAUTIFUL GIRL, said the cheesy note attached to it. We shared awkward conversation until we arrived at a restaurant that was closed. He frantically called his dad for alternatives…and we wound up at an Irish pub with a brass band “serenading,” but mostly embarrassing us. He couldn’t take his eyes off me, but the tension grew as he kept trying too hard. After dinner he drove me to a Festival of Lights at a park. The traffic was insane and things were shutting down—again he was too late. This is when he decided to inform me of his “sexual-progress diary.” “It’s where I jot down how I did, and what the reactions were. What, you don’t keep one?,” he said. “No,” I informed him, not believing this was happening. I asked to be taken home—”I have to study” was my ready-made excuse. He purposefully went the wrong way, then insisted I see his apartment. “I’ve cleaned it up!” he boasted. I refused. We ended without a kiss or a hug. “You know, if you ever want to, uh, hook up…call me.” Guess what? I didn’t!—Jill, Pilsen

Ex rated
I responded to Katie’s dating ad on Craigslist, and after a few days of correspondence, we decided to meet. However, since this was, according to her, the first time she had gone out on one of these online dates, she wanted each of us to bring a friend along. The four of us met for a few drinks at the Blue Line in Bucktown and had a great time. Katie then suggested we go to her favorite bar, Lottie’s. As we were walking in, Katie’s friend noticed Katie’s ex-boyfriend in the bar. We nonchalantly found a table at the back, trying not to look at the ex. After getting our drinks, we settled in at the table for a few minutes and picked up the conversation—until the ex-boyfriend suddenly towered over our table, said hello to his former girlfriend and proceeded to pour a very tall gin and tonic on her head before walking back to the other end of the bar. My friend and I were sitting across from each other sharing looks of disbelief, not really knowing how to respond beyond handing her a bunch of cocktail napkins. As Katie tried to get all the ice cubes off of her, her friend went over to confront the ex-boyfriend, who rudely dismissed her with a hand to the face. After Katie dried off, we went to another bar for one last drink, but we just sat there not really knowing what to say. We didn’t go out again.—Tom, Andersonville