Navy Pier's Centennial Wheel decked out for Spinning Singles

The TV news reporter kept asking everyone the same stupid question: “So, what are you doing here?”

A man dressed in a casual blazer and jeans whose name was probably, but not certainly, Doug (I was going by the handwritten name tag pinned to his lapel) smirked into a camera, leaned into a microphone, and said: “I’m on a Ferris wheel in the world’s greatest city. What could go wrong?”

Doug’s answer was meaningless but perfectly reasonable. The intention of Navy Pier’s second annual “Spinning Singles” speed dating event last month was more clear than Lake Michigan on a sunny summer day. All of us had journeyed here to mingle with attractive people while soaring on an amusement park ride, then drinking on a yacht docked in the lake. What more did you need to know, TV lady?

This wasn’t one of those anti-singles parties that defiantly celebrate their resistance to Valentine’s Day’s Dracula-like suck on America’s attention. This was the opposite. This was V-Day on steroids, primed to shock and awe its participants into romance. The evidence was everywhere: Rose-colored tissue paper littered the place. Servers freely handed out glasses of red wine. And my god, the Ferris wheel! The pink lights affixed to the  Centennial Wheel (including a LED-lit cartoon heart the size of a SUV on the central hub) shone so brightly that everything around it looked dipped in Pepto-Bismol.

Crass, perhaps, but so is our culture’s obsession with performative courtship, the kind in which two parties bludgeon each other with cloying romantic gestures like, well, riding a 200-foot-tall pink-hued ode to true love. That thought didn’t occur to me until later, because when you’re busy chatting up a bunch of randoms on a Ferris wheel in hopes of finding the One, it impairs everything beyond a conversation-heart level of thinking. Or discussion, for that matter.

Spinning Singles was a speed-dating mixer that could have easily been advertised as the world’s most dizzying (and pink) group job interview. Here’s how it worked: The 90 participants—45 women, 45 men—were assigned a number, then packed six at a time into each of the wheel’s 41 gondolas to engage in fun and flirty conversations while ascending into the night sky. Meet someone that piqued your interest and you were encouraged to slip him or her a contact card from a small deck distributed during an earlier orientation session. Each had the words “Let’s Connect!” printed on the front along with a space to write in your name and contact information.

Exchanging business cards may not be the most sentimental of gestures, but brutal efficiency is essential when you’ve got 12 minutes before being shuttled off into the next car. Every time the wheel rotated the full 360 degrees, we’d part ways with our bite-size group dates, move to the next car, rinse, and repeat. It wasn’t just the Ferris wheel that constantly spun, in other words, it was also a sense of social equilibrium. Wait, who is this I’m looking at again?

Each speed date lasted a full revolution of the Ferris wheel (about 12 minutes)
Each speed date lasted a full revolution of the Ferris wheel (about 12 minutes)

I was stuck staring at the same pair of guys for much of the night. The rules called for the “spinning singles” to swap gondolas after each successive spin in order to meet with three new members of the opposite sex, but oddly enough, we remained with our same-sex “competition” (let’s face it, this event was heteronormative AF) for the entire time. I got to know my dude datemates pretty well over the course of the night as a result. That wasn’t necessarily a bad thing. John and Michael, a pair of preppyish roommates in their early 20s were charming wingmen (wheelmen?), and telegenic enough that I began to suspect that Spinning Singles was simply serving as a warm-up for a reality-TV dating show they’d appear on in the future.

It helped matters that we were surprisingly comfortable riding a Ferris wheel on a harsh Chicago winter night. When the Dutch-designed Centennial Wheel was installed in May 2016 as part of the pier’s larger renovation project, most of the attention focused on its size—at 196 feet, it was nearly 50 foot taller than its predecessor. I’d argue that the addition of the bigger, flashier navy-blue-colored gondolas was the more significant change. Each car’s climate-controlled interior was outfitted with padded seats, TV screens, and speakers, and it made the experience of the ride feel more like being in the back of a limousine, except that it traveled vertically instead of horizontally.

Had we been served booze (it didn’t flow freely until later on the boat) or provided with the right soundtrack, we might have also believed we were in a tiny gyrating VIP room at a nightclub. Instead we talked to strangers in sober silence—a stark reminder that modern urban dating is bizarre and alienating.

During my first “speed date” experience, we interacted almost solely through icebreakers. It felt surprisingly old-fashioned, like a secular church social. Three men were sequestered on one side of the gondola and three women on the other side, and they had polite conversations like this:

“So what do you do?”

“I’m a first-grade teacher. Live in the west suburbs.”

“Cool, I’m in merchandising. I live in the Loop.”

“Oh? I’m in Old Town, work in logistics. You know—supply chain.”

This wasn’t exactly patter to make your heart go flutter (or beat at all for that matter). I felt the need to shake things up on my second go-around on the big wheel of love.

“Sorry, Devon, I couldn’t hear you,” I said to the woman lounging on the padded blue seats on the opposite side of the gondola. “Did you say you were a meth dealer?”

“No, event planner!” she replied with a laugh.

“Actually, I know how to make meth,” said her seatmate, a woman whose name tag pinned to her black top identified her as Elliott. Was she serious? Devon and Elliott were both in their late 20s, tallish and blonde, with easy smiles and rat-a-tat-tat banter. They struck me at first as sisters or an improv comedy duo, but they told me later they were just close friends. Regardless, they seemed ready to break out of this stiff format. 

The Spinning Singles orientation inside the Navy Pier Crystal Gardens
The Spinning Singles orientation inside the Navy Pier Crystal Gardens

“So, what about you?” John asked the shy college-aged woman sitting side-by-side with Devon and Elliott. “Who are you, and how did you find about this?”

“I’m Brandi,” she said. I can’t recall what she said next because, well, have you ever tried to remember how a dozen people you met at a party answered the same innocuous question?

That’s why John was a goddamn hero. His everyman charisma and Good Will Hunting-era Matt Damon looks convinced me he’d one day survive a crash on the surface of Mars by becoming a makeshift potato farmer. On this night, John bravely guided the nervous crew of a more modest kind of vessel by prompting new questions and intervening almost every time there was a hint of an awkward pause in the conversation.

Still, Brandi only spoke a handful of words. The conversation largely ping-ponged between the two pairs of friends and me, our breath fogging up the safety glass keeping the cold air out. I learned that Elliott was a scientist who wasn’t bullshitting about knowing how to make homemade meth, though she warned that she’d never put that knowledge into practice.

At some point, I let it slip that I was recently single after a breakup. “Dude, are you like OK to be here?” Elliott asked me. We all laughed. We’d earned a small achievement as a group: we’d created a modicum of intimacy in 12 minutes together.

“It was a fun group to talk to,” John admitted as we strolled to the yacht from the Ferris wheel. “Everyone puts up a front. Sometimes it felt like we were on a job interview where you’re thinking a lot about what you’re going to say. But that second group was so relaxed—it was cool.”

John also confessed two additional facts:

  • His brave facilitating skills were alcohol assisted. He and his roommates had slurped down three drinks beforehand to temper their nervousness.
  • He had a thing for Brandi.

“My end goal is to get her number by the end of the night,” he said. 

That seemed eminently achievable after we arrived at the landlocked boat docked to the pier. The yacht promised everything that the Ferris wheel lacked: alcohol, thumping bass lines, dim lighting. These elements exist in almost every place singles mingle for a reason: our senses need to be tricked into believing that looking for love by making small talk with a room of random strangers is a perfectly natural thing to do.

For an hour and a half, we the singles-who-no-longer-spun sipped boozy drinks, nodded our heads to the DJ’s dancey tunes, and chatted in the hull of the ship. Now all 90 of us were trudging the length of the pier through the snow to our separate ways. Elliott, Devon, and I were laughing at the ridiculous antics we’d witnessed. The drunk woman who kept chain-eating shrimp! The guy who faked a southern accent to test-market it with the ladies! (Spoiler alert: it did not go well.) And what was up with that dude who kept approaching small bands of women with the line “Hey! Where are we all going after this?” (That did not go well, either.)

Before they jumped into a cab, Elliott handed me her “Let’s Connect” card—her number scrawled on it in blue ink. “That was hilarious. Let’s hang out again sometime,” she said.

Moments later, while biking on Grand Avenue, I caught up to John and Michael and asked John what had happened to his quest to ask Brandi out.

“She said yes,” he said with that big, dumb Matt Damon grin. “We’re going out next week.”

At the beginning of this blustery night, I couldn’t help but look up at the Ferris wheel and see a depressing supersize metaphor: Love comes with a steep admission fee, spins you in the air, and then ends abruptly.

But that cynical thought had melted down, replaced with a pearl of wisdom I’d heard earlier from possibly some great philosopher: “I’m on a Ferris wheel in the world’s greatest city, what could go wrong?”

What was his name again?