An overeager cowboy. A man with a broken penis. A guy who gleefully recounts tales of his cocaine arrests. Readers went on terrible first dates with these freak shows so you don’t have to. Illustration by David Opie
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Lonesome cowboy
I took a ballroom-dancing class in college (long before the Dancing with the Stars craze). The only cute guy in class was also the best dancer, and since I was the best of the ladies—no great compliment, since most of our classmates couldn’t hold a beat to save their lives—we shot each other relieved looks when we occasionally wound up as partners. We didn’t talk much between rumbas, cha-chas and waltzes, but his tall, broad-shouldered physique wasn’t lost on me, nor his chivalrous demeanor, nor his Wranglers and gray T-shirts that fit oh-so-well. And damn, that guy could move his hips. 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
