Shitty First Dates: Casey

Shitty First Dates: Casey

By Brett Dworski

First dates suck. For some, the pressure to find a mate for life — or at least for the time being — pounds away like a woodpecker drumming its beak. These are the people who snarl at their Facebook feeds full of friends getting engaged or having children. Dating is awkward, uncomfortable and, most of the time, miserable. Over the next few months, I will examine some of my all-time worst romantic outings to show that finding “the one”, in fact, blows.

Welcome to Shitty First Dates.

My mother was thrilled when I told her I set up a date set up through J-Swipe — also known as Jewish Tinder.

“Yay Bretty! What’s her name? Where’s she from? What does she do?”

Four years prior, Mom asked my sister, Jordan, the same questions during her tenure with the dating app. Two days later, Daniel Schwartz got a LinkedIn notification saying my mother had viewed his profile. Jordan never saw Daniel again.

“Slow down, ma,” I said. “You’ll find out after date five, if I get there.”

I fell four dates short.

Casey and I met for dinner on a late-winter Wednesday at Quartino Ristorante, a bustling, old school Italian joint in Chicago’s River North neighborhood. She had light brown hair that reached her shoulder blades. She wore blue jeans, black boots and a black North Face fleece that screamed 2006. We hugged and sauntered to our table.

I ordered the Brodetto al Frutti di Mare, a classic seafood and pasta smorgasbord. Casey went the more adventurous route and requested plain rigatoni with a side of marinara.

“I get this every time I go out,” she told me. “I guess you can say I’m picky.”

Her flat taste buds paled in comparison to the way she ate. Casey swooped the end tine of her fork through the hole of each individual noodle. She then dipped each noodle in her puddle of red sauce. She grinned with each bite as if she’d tasted Kobe beef slaughtered from God’s own herd of Kobe cows.

“Want some?” she asked. “It’s delicious.”

Politely, I accepted. I speared a few noodles with one poke and reeled the fork towards my mouth.

“No, you can’t do that,” she said. “You have to swoop it.”

She wasn’t kidding.

“That’s how I was raised,” she said. You have to swoop it.”

Oy vey.

Nothing’s more appreciated than when a lady offers to pay for herself on the first date. Not that I always let her, but the mere reach for her Visa and amiable attempt to place it on the table basically shouts date number two.

Casey flopped here. I wasn’t even going to ask her to split the meal, since her noodles basically cost nothing, but I would’ve appreciated the gesture. Her back pocket was lonely as ever that night.

“Want to get drinks?” she asked.

We went to Pops for Champaign, another bougie River North staple. I snagged an open booth in the corner of the noisy bar. Casey ordered a vodka cranberry with Tito’s while I opted for the Nitro Milk Stout.

For a brief moment, things were swift: Casey and I discussed our passion for the Bulls, our desires for international travel and the fact that both of our fathers have completely white beards and full heads of black hair (no dye). Maybe Casey wasn’t so bad after all.

But then she saw my dance moves.

The song “Friend Zone” by Thundercat blasted on the surround sound speakers — an ironic tune for the occasion. I bobbed my head and swayed my shoulders like John Travolta in Saturday Night Fever. Casey swelled with embarrassment.

“Oh my God, please stop,” she squawked. I thought she was kidding, so I bumped my shimmy to turbo drive. She put her left hand over her mouth; her eyes widened.

“You need to stop right now!” she said.

I stopped. And to my surprise, Casey invited me back to her apartment. We Ubered to her Gold Coast high rise and entered the front door. I tipped my nonexistent hat to the doorman and he tipped back. We reached her eighth floor, one-bedroom palace and sat on the couch.

Casey was an awful kisser. Her lips danced on mine like she was guessing the flavor of a cocktail while her tongue flopped to every corner of my mouth with no rhythm whatsoever. Nonetheless, it was a kiss — something I hadn’t experienced in a while.

After slopping for about half an hour, Casey said she was tired. And rightfully so, since it was 2:30 a.m. Instead of inviting me to her room or even letting me crash on the couch, she told me to leave. Straight up kicked me out, forcing me to trek back to my parents’ house in the suburbs. 

And I did, gracefully. And we never spoke again. 

I crept into my childhood home 45 minutes later. My mother was still awake, anxiously waiting to hear about my date.

“Bretty! How’d the da—”

“Don’t ask, Mom. Don’t ask.”

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