The Most Depressing Date in Chicago History WHEN DOVES CRY: Guy meets Girl. Girl humors Guy with date. Homeless Man produces shoebox.

As Mel Brooks said, “Tragedy is when I cut my finger. Comedy is when you walk into an open sewer and die.” This may explain my fascination with horrible dates. In honor of Valentine’s Day, I submit the following true tale as the Most Depressing Date in the History of Chicago—but if you think you’ve got one worse, tell me about it in the comments section below, you poor bastard.

* * *

Wicker Park, 1990. Hypodermic needles float in the fountain on Damen Avenue. Packs of wild dogs roam North Avenue, befouling the empty storefronts that would a generation later become boutiques and cafés.

A pretty girl with a life-size tattoo of her own skeleton on her back walks into Dreamerz, a gritty punk club on Milwaukee Avenue, sending jolts of lust through the bouncer’s veins. She’s tough, smart, and more into art students than bouncers. But our guy—let’s call him Guy—is a quirky romantic who only wants a normal conversation in a locale where his peculiar charms aren’t drowned by the 100-decibel hardcore slash of some jerk-off guitar bashers from Detroit. Wanna get a bite to eat later? he asks. Nope, she says.

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For weeks she keeps coming to Dreamerz, and he keeps asking, so fierce is his passion. Whether charmed or simply worn down (he doesn’t care which), she finally relents. Unfortunately, all she relents to is a late meal at the bleak Mexican hole across from the club. Guy and Girl, one nervous, the other indifferent, get two orders of quesadillas with avocado, the only thing any customer is brave enough to order in the joint, and settle in at a pocked Formica table.

For Guy, even close proximity to Girl is electrifying. He’s just beginning to pierce her hard-bitten exterior—making her laugh, even!—when a homeless man named Willie approaches. A notorious neighborhood loony with jaundiced eyes, a sodden trench coat, and a nickname too awful to print here, Willie is known for his shopping cart filled with stuffed animals and other scavenged items. Guy has always been gentle with Willie, but the slightest hiccup could topple this fragile date, so Guy kindly tells him to go away.

That’s when they see the shoebox.

A gift for the pretty lady, Willie burbles through jagged teeth, and lifts the box’s lid to reveal a headless pigeon. He has artfully arranged a T-shirt under the corpse, its skinny legs jackknifed in the air. Other than the translucent cords dangling like crystal noodles from the bird’s mangled neck, it’s a strangely sterile tableau.

A good bouncer is all about protection. To defend his date, Guy instinctively drags Willie from the restaurant, and he returns to his table feeling triumphant. He finds Girl crying, not over the decapitated-fowl coffin lying next to their quesadillas, but rather at her suitor’s callousness. “The man gave the only gift he could,” she moans, and no amount of apologies can deflate her umbrage. Guy’s tiny crack of an opening slams shut.

Guy goes back to his job, back to lonely. Not long after the pigeon episode, he spots his nemesis, a smug ponytailed butterball (who will go on to be a fairly successful Hollywood producer), in the company of Girl. Then Willie dies. “The dead bird wasn’t like some big, terrible omen,” says Guy, now 43 and living in Old Irving Park. “I just didn’t think she wanted it near the quesadillas, that’s all.”

Happy Valentine’s Day, lovebirds.

Illustration: Michael Park

This article appears in the February 2011 issue of Chicago magazine. Subscribe to Chicago magazine.

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