‘I Asked the Guy Why Are You So Fly?’ by Megan Stielstra

‘I Asked the Guy Why Are You So Fly?’ by Megan Stielstra
Photo by Julie Sadowski
‘I Asked the Guy Why Are You So Fly?’ by Megan Stielstra
Photo by Julie Sadowski

‘I Asked the Guy Why Are You So Fly?’ by Megan Stielstra

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Megan Stielstra is a writer, storyteller, and literary director for 2nd Story, Chicago’s urban storytelling series. She’s performed for the Goodman Theatre, the Chicago Poetry Center, and National Public Radio. Her writing has been performed by the Serendipity Theatre Collective, Theatre Seven of Chicago, and Bohemian Archeology in New York. She teaches in the Fiction Writing Department at Columbia College and is a lecturer in creative writing at the University of Chicago. Her first book, Everyone Remain Calm, just came out last week. You can buy it here and learn much more about Megan here.

Megan Stielstra at Grayscale Studios (Photo by Julie Sadowski)

“Thirty is the new Twenty,” Bridget told me on my Thirtieth birthday. We were having brunch at one of those very hip places, with honeydew mimosas and servers who are really fashion models. Makes you wonder, how do they not spill honeydew mimosas all over their expensive designer clothes? Why do they wear expensive designer clothes to serve breakfast? Why do people wear expensive designer clothes to eat breakfast? Even Bridget had on an electric pink Juicy jumpsuit. And a spray tan. Which made her look orange. Pink and orange. Which is maybe the new black, like Thirty being the new Twenty.

Bridget turned Thirty a couple months ago since then she’s developed a few—how should I say this?—quirks. The spray tanning, for one. A particular fondness of the word asshat (as in, “Of course we’re having brunch on your birthday, Diane, don’t be an asshat!”). The Valley Girl accent is another. She sounds like Julie in the movie Valley Girl: Encino is, like so bitchin’! Twenty is, like, the new Thirty! which apparently Bridget found comforting, but not me.

I was in no hurry to replay my Twenties: the indecision. The self-loathing. The dating.

On my last date, the guy talked about camping in Wisconsin, and I made a list on my napkin.

How This Guy and the Last Five Guys I’ve Gone Out With Are Exactly the Same:

1) They camp in Wisconsin;

2) They listen to the Foo Fighters;

3) They drink imported beer;

4) They have complex relationships with their mothers;

5) They have responsible corporate jobs;

6) I had sex with all of them (about which I could write a whole other sub-list titled: How This Guy and the Last Five Guys I’ve Had Sex With Have Sex in Exactly the Same Way).

“Happy birthday!” Bridget said. She ordered two more mimosas from Kate Moss and handed me a card. On the front were tiny pictures of different men, each about an inch wide so several could fit onto the paper. Over them was printed: For your birthday, I wanted to get you thirty hot guys! I opened the card and read: So I DID! and beneath it, in smaller writing: Fastdater, Incorporated.

Bridget was smiling, waiting for me to rush over and hug her. In our Twenties, she and I hadn’t been the hugging kind of friends, but now we were in our Thirties, which were the new Twenties, and I was supposed to hug and wear shimmery lip gloss and know what Fastdater Incorporated was.

“So I got the idea ’cause I was dating Lance who was a total asshat and this girl I work with Stephanie said, Come with me speed dating! and I went and was like, Wow, and I know how shitty it is to turn Thirty and be alone but this is so much fun!” and then she jumped up, ran over, and hugged me. She smelled like the entire Marshall Fields counter, and I wondered how a number—a three and a zero—could turn my seemingly normal friend into this orange huggy thing. Would it happen to me? Come midnight, would I also turn into a pumpkin?

“Bridget,” I said into her hair. “What exactly is speed-dating?”


“This is how it works,” said Tina. She was addressing the sixty Fastdater customers crowded into Leopard Lounge, a dark, smoky bar with—surprise!—leopard-spotted upholstery. The candle-lit tables had been lined up in rows around the room, each with two chairs and a number, one through thirty. “Everyone has a badge,” said Tina. Hers said Hi my name is Tina. Mine said #12. “You’ll meet your first date at the table that corresponds with your number, and you’ll have three minutes until I ring this bell.” She demonstrated: ping ping. “Then, women stay seated and guys move one table over, again and again ’til everybody’s met everybody. Everybody ready?”

Initially, I wasn’t going to do it. But since my birthday, everything had sucked. Not because something had happened; because nothing had happened.

How Every Day Since I Turned Thirty Has Been Exactly the Same:

1) Traffic sucks;

2) Edit copy;

3) Corner Bakery/chopped salad;

4) Edit more copy;

5) LeanCuisine/America’s Next Top Model;

6) Can’t sleep/Sominex, an over-the-counter sleeping pill which knocks you out, but keeps you in this perpetual half-sleep stage. You move slowly. Colors are dull. In conversation, the other person says murp murp mrrrruuuup.

I needed something to wake me up, a bowl of ice water in my face. So far, Fastdating was doing the trick: the Technicolor leopard print. The vodka tonics. The overwhelming possibility.

I sat at table #12 across from a good-looking guy in his mid-Thirties; expensive suit, bourbon on ice. Nice, I thought. He’s got all his hair.

ping ping

“Bruce/divorced/tax attorney/scuba,” he said, all one word. “What’s your lead?”

“My what?”

“Lead, lead, you’ve got to have a lead-in question, like What’s your favorite book, What music do you listen to, Do you like sushi, whatever, something to jumpstart conversation or else you’re going to waste our whole three minutes.”

“How many times have you done this?” I asked.

“Look, we’ve pissed away a full minute already. You got a lead yet?”


“Let’s go!”

“Uhm… What’s your favorite book?”

He groaned, like I’d asked the stupidest thing in the entire universe, and then talked nonstop about The Seven Effective Habits of Whoever until the bell rang. On the table in front of us were pencils and paper. He grabbed them and started writing.

“What are you doing?” I asked

He groaned again. “You write what you think of the date next to their number. When tonight is over, you enter the numbers you like on Fastdater’s website, and if we both entered each other, then we go out for real.”

“Oh,” I said, taking paper and pencil. Next to #12 I wrote: Asshat.

ping ping

#11—Tall, Stubble, Polo shirt—sat down across from me and extended his hand. “Eddie,” he said. “I’m a copywriter.”

“Me too!” I said. We shook.

“What music do you listen to?” he asked. “I like the Foo Fighters.”

Next to #11, I wrote: He likes the Foo Fighters.

ping ping

“Hi,” said #10. “I’m James. What music do you listen to?”

#10, I wrote: Also Foo Fighters.


#9: Foo Fighters.

#8: Foo Fighters.

#7, 6, 5—

ping ping

“Isn’t this weird?” said #4. “Meeting people like this?”

“I know!” I said.

“My brothers got me a certificate,” he said. “They thought I needed to get out more.”

“My friend bought one for me!” I said. This was looking up. I checked him out: older, past Forty maybe; in good shape, like he had a personal trainer. “It was a birthday present,” I told him.

“Yeah?” he said. “Which birthday?”

“The big one,” I said. “Thirty.”

“Oh,” he said. “I don’t date women over twenty-five. Too much commitment.”

#4, I wrote. Asshat.

ping ping

“My favorite book?” said #3. “The Harry Potters. I think she’s developing a global community and—”


A Million Little Pieces. I’m an addict myself and—”


“My favorite book? Why, the Bible of cour—”

ping ping ping

“Nice to meet you,” said #30. He was very thin, in a suit and fuzzy winter hat. We talked for a while and it was good. I could see this guy again! I thought, and he said, “I should tell you I have cancer.”


“I was diagnosed a couple months ago.”


“I have a hard time talking about it, so I do speed dating to practice. You can say anything to a stranger, you know.”


At that point, I was done. This was ridiculous, it was bullshit, me and my Sominex are outta here! I thought, standing up to leave at the same time #29 sat down.

ping ping

This guy was—first—black—and second—big, wearing a two-sizes too-big baseball jersey and a backwards baseball cap. He had a thin stubble moustache over his upper lip, and around his neck were four or five thick chains with different things dangling from them. He was like no one I’d ever seen in person—this guy was a music video or an album cover—a total one-eighty from every guy who’d sat across a table from me.

“Wassup,” he said. His voice was deep and scratched. “I’m Tone.”

“Hi, Tony,” I said, sitting back down. “It’s really dark in here, why are you wearing sunglasses?”

This guy leaned forward across the table and beckoned me closer. He spoke low, like he was telling a secret. “I don’t want to be recognized,” he said.

“Are you hiding out?” I asked, thinking The feds?

“No, baby! I got fans, you know, and I don’t want to be bothered with all that right now.”

“Okay then,” I said. “What’s your favorite bo—”

“Okay,” he interrupted. “You really want to know who I am?”

I nodded, and he reached up and lowered his sunglasses so I could see his eyes. We stared at each other for a minute—me searching my memory, searching, searching, nothing—and he put the glasses back. “See?” he said.

I shook my head.

“Okay, okay, listen,” he said, and he picked up a pencil and held it like a microphone: “And we go a little something like this, hit it!”

He sat back, giving me this look like Uh-huh! but I still didn’t know.

“Were you living in a barn in ’89? Didn’t have a radio in the house?”

“I was fourteen in ’89,” I told him. “I listened to Debbie Gibson.”

He slumped back in his seat. Through the candlelight and the vodka, I thought he looked sad. I thought I could make him feel better. “Sing a little more!” I said.

“Naw,” he said. “I can’t.”



“Come on!” I said, and before I could even get the words out, this guy whipped a boom box out from underneath the table and pressed play.

As the bass and drums got going, he stepped first onto his chair and then the table. I was eye-level with his knees, his baggy denim and hiking boots stepping side-to-side with the music.

“Hey,” I yelled up at him. “Is that a cowbell?”

He looked down and grinned as a spotlight appeared out of nowhere and locked on him.

All around us, the Fastdaters stared. Some were embarrassed and looked at the floor. Some tried to continue their dates as through nothing was happening. Some scowled and others laughed, it was all so completely ridiculous: Tone on the table; the three minute dates; this relentless, sometimes desperate search for love. Still, we were all here. We’d always be here, because—if we’re really being honest—is there anything more important?

That’s when #30 stood up. Remember #30? The fuzzy hat? The cancer in his bones? He was just one table over so I had an excellent view: he moved his body, slowly, side-to-side. He lifted his arms, swirling them in front of him like treading water.

Dancing. He was dancing.

“What’s he singing?” asked the girl next to me at table #11.

“Funky Comedina,” said her date.

“What’s a comedina?” I asked.

“A medina is the oldest part of a North African city,” #11 said, and, in answer to my look: “I’m a geography teacher. But I don’t know what a comedina is, maybe a—“

Cold Medina,” said her date. “Funky Cold Medina.”

“Coming up,” said the bartender.

“Excuse me,” said the girl on my other side; #13. “I take issue with this song. He—” she gestured at Tone, dancing on the table— “is advocating the use of GHB, also known as the date rape drug. He slips this—” she put up her fingers in air quotes— “‘medina’ into women’s drinks in order to—” again with the air quotes— “‘get them on their back.’”

For some reason, I felt the need to defend him. “The only ones drinking medina in the song are dogs and a lady named Sheena.”

The bartender set shot glasses down on our table. “What’s in them?” asked the guy at 11.

“Vodka, Southern Comfort, Blue Curacao and Cran,” said the bartender.

“Here,” I said to the girl at 13. “Have a shot. Loosen up.” And then I did the shot.

And then I did another. And another, and everything became surprisingly clear.

“Everybody!” I called out, “Have a drink! Medinas all around!”

That was the beginning. By the end, we were all up and dancing: the Asshats and the Foo Fighters, all the girls in lingerie tops and expensive jeans, one of us looking so much like the other.