How I Used Algorithms, Data, and Lists To Game Online Dating and Find My Match

What women really think about news, politics, and culture.
Jan. 31 2013 5:33 AM

Data: A Love Story

The algorithms, statistics, charts, and lists I used to game online dating and find my match.

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“Of course not,” I said back as he punched some numbers into his phone and put it up to his ear.

“Yes?” he began. “Yes, that’s right. It’s what I said earlier.”

There was a long pause, then a sigh. “Yes, that’s exactly what I meant.”

Another pause.

“Fine. Yes, that’s correct,” he said. “OK, bye ... ,” he trailed off, putting his phone back in his pocket.

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“Sorry,” Jay said. “That was my wife.”

I had no knowing glance for this.

Jay immediately qualified what had just happened with a long-winded, confusing explanation: Technically he was still married, but he and his wife were on a trial separation. They’d been seeing a therapist who recommended that they each see other people. He was sure their marriage was over, so he decided to use Match.com to look for new companionship. But since there was no checkbox for “trial separation,” he listed himself as single.

As he continued to rattle off various other issues and concerns, I felt increasingly numb. Did he just say that he’s married? What just happened? Maybe the bartender accidentally used real gin in my drink? I stared at the glass, looking for signs of alcohol.

“We got married too early,” he rambled. “We don’t have any kids, so I think now’s the best time to split up.” As he carried on and on, complaining about how she didn’t understand his stress at work, I noticed a strand of long blond hair clinging to his shirt, just above his wrist. Farther up, there was a pale band of skin around his ring finger. They must have spent the weekend together at the beach, out in the sun, I imagined. She’s probably very pretty. Nice, even.

“She’s just prying like she always does,” Jay said. “We are supposed to date other people!”

I shook my head, involuntarily trying to unhear what he’d been saying. “You’re fucking married?” I shouted. “Married?” I couldn’t look at his face as he whined about his wife. This time, I skipped the bathroom. I didn’t bother with the email, since I hadn’t built “Forgot to tell me he’s married” into my rating system. I reached across him, picked up my bag, and bolted toward the door.

Once outside, I pulled out my iPod and scrolled through to find George Michael performing “Don’t Let the Sun Go Down on Me” live with Elton John during a 1991 show at Wembley Stadium in London. I turned up the music as loud as it would go, shoved my hands in my pockets, and started walking.

Fucking Match algorithm! The one fucking time Match sets me up with someone who I am actually compatible with, I get screwed by the user data. Fucking married asshole!

As I neared the steps to my apartment building, I fumbled for my keys, which by now were tucked in one of the dark pockets of my massive bag. I pushed aside my laptop, realizing that it had never occurred to me to visit the bathroom to track date data. Instead, I’d fantasized about showing him my spreadsheet of horrible dates. We’d laugh about what I’d done, but as a journalist he would appreciate the thought and dogged reporting I’d applied to my data analysis.

I walked up the flight of stairs, put my key into the lock, and opened the door to my dark apartment. I’d been duped into falling for a cheating liar. What was the point of this exercise?

I threw on the lights and stood in the kitchen, staring at my reflection in the glass-paneled cabinets. Jay hadn’t tried to high-five me. He drank espresso instead of beer. He asked thoughtful questions and seemed genuinely interested in my answers. He seemed so fantastic, so eerily perfect. Except that he was fucking married.

“All things come to she who waits,” my relatives would tell me every time I saw them. Maybe they were wrong. Maybe my mom was wrong. Wasn’t it possible that patience has no bearing on whether or not someone finds love? Everyone I knew was giving me the same advice: Date everyone! See what’s out there! Give these men a few chances before telling them no! A new chart came to mind: 

WEBB-1-Crappiness

“What if Jay was the one for you?” I could hear my grandmother asking in her wobbly old Jewish-lady voice. “So what if he’s married? He’s not happy. He’s not happy, he gets a divorce. Then he gets married to some other girl, who has your babies with him. And then what? You have no family. You have no husband. You have no life. Was he Jewish? What kind of a fercockta name is Jay?”

I watched my reflection contort as I thought about Jay and this other woman and their perfect children. Just beyond my crumpled brow, I noticed a glint of foil wrapped around the neck of a wine bottle. The previous tenant had left it for me as a thank-you for helping her out of her lease. It was still decorated with the orange ribbon she’d curled and tied around the foil. The bottle had been collecting dust for months. I didn’t typically drink by myself at home, and I never brought any dates here. But after Jay, I wanted a corkscrew.

I rifled through the utility drawer first, pushing aside a pile of rubber bands and some old pens to see if I could find an opener. A lighter with a transparent green case was stuffed in the back along with a pack of matches.

“I’ll need that,” I muttered aloud and shoved both into my pocket.

I looked back up at the cabinets, realizing that even if I did find a corkscrew, I no longer owned any wineglasses. Henry had kept all of them, along with most of our kitchen equipment. I’d taken our television and bedroom set, which seemed like practical choices at the time. I’d been too busy at work to replace my glasses and plates. And anyway, most nights I either picked up dinner on the way home or met up with friends. Alone on the shelf was a 16-ounce Three Peckered Billygoat Coffee travel mug I’d bought a year ago during a family trip to Alaska. It was better than drinking straight out of the bottle, I figured. As I reached for it, I saw the corkscrew hiding in the very back of the cabinet.

I unwrapped the foil, shoved the corkscrew into the top, and tried to pry the cork out. Why are these things so fucking difficult to open? I pushed and shoved until half of the cork broke free and plopped into the wine below. I didn’t care. I filled my mug halfway, stopping just beneath the third pecker, and watched bits of cork slosh around as I walked toward my patio.

The pack of Marlboro Lights was just where I’d left it, between a hurricane candleholder and a mostly dead aloe plant. I’d bought cigarettes last week, vowing to have just one. The pack was now a quarter empty. I tipped it over and slid one out. I reached into my pocket for my mobile phone, dialed Hilary, lit my cigarette, and inhaled.

“Weren’t you supposed to go out with Jeff Goldblum tonight?” Hilary answered. She was at a dinner party at a friend’s house. Her fantastically amazing friends, Eric and Ralph, had slaved away cooking a lovely meal for eight sophisticated guests, who also happened to be wildly interesting and fabulous.

“Just go somewhere quiet,” I sighed.

“OK, just give me a minute,” she said. I heard the brush of her clothes against the phone and muffled conversations coming and going as she passed by her dinner companions. She pulled the door shut behind her.

“So what happened?” she asked.

“He’s married!” I said, getting right to the point.

“No!” she shouted. “Journalist Jeff Goldblum is married?”

“Fucking married!” I shouted. I told her all about how good he looked. How we’d bonded over our shared irritation at the copy desk. He asked the waiter thoughtful questions about espresso! He thought it was amazing that I’d lived in Japan!

“You’re right,” she empathized. “Match doesn’t really have an option for ‘lying about my relationship.’ ”

“Lying asshole is more like it,” I said, exhaling smoke into my phone by accident.

“You’re aware that our mother has cancer, right?” she asked.

“It’s just once in a while,” I said. “Don’t I fucking deserve a cigarette after tonight?”

“I’m just saying. ... You should lay off. It’s not good for you,” she said. I could hear a toilet flush, then water swirling violently in the background.

“Are you peeing? Are you going to the bathroom while I tell you the tragic details of my life?”

“You said ‘go somewhere quiet’!” she said. “I did. Eric’s bathroom. I’m at a dinner party.”

“I don’t have the endurance to go on any more dates,” I sighed. “I’m done. I’m canceling all my memberships to every fucking dating site.”

“Don’t do that,” she said. “Listen, you just have to keep trying. I promise you, there’s someone out there who’s great and good-looking and not married. And he’ll somehow appreciate your very bizarre fashion sense and weird neuroses.”

“Doubtful,” I replied.

“Do you remember how we used to watch Mary Poppins when we were little?” she asked. “Those two kids, Michael and Jane. They can’t get along with any of their nannies. They go through one after the other—they hate all of them. Does that sound familiar?”

“I’m not a fucking child, and I’m not trying to find a nanny.”

“Just hear me out,” she said. “Remember how one night, they write an ... advertisement?” she said, drawing out the ver with an exaggerated British accent. “They wrote The Perfect Nanny at the top and then made a big list of everything they wanted?”

We’d watched that movie a million times when we were little. One week, we decided to re-enact the Supercalifragilisticexpialidocious scene using our stuffed animals. So we rewound, listened, paused, practiced, and repeated the song over and over until we finally warped the VHS tape. Perched on the toilet, Hilary started singing as quietly as an opera singer is able: “Have a cheery disposition. Rosy cheeks, no warts, play games, all sorts ...”

I was humming along with her at this point.

“Remember?” Hilary said. “They make the list; then Mary Poppins appears.”

“Right ... ,” I started.

“So maybe you just need to make a list and a husband will magically appear,” she said. “With a fabulous black satchel and a top hat and cane. Actually, that sounds just like Eric. He would totally wear a top hat ...”

In that moment, I realized why I wasn’t finding a good match, and indeed why all single people in the online dating world were struggling. Algorithms weren’t at fault. Neither was bad data. We weren’t making Mary Poppins lists. We’d never sat down and made a giant comprehensive list of exactly what we wanted—required!—in a mate.

Dating sites relied on rudimentary information. Do I smoke? Do I want kids? Do I prefer a specific level of education? Then the sites matched us with others who had similar data points. But in attempting to make dating sites applicable to the widest possible user base, all of the questions had been made far too generic. I wasn’t going on great dates because I wasn’t being specific enough about what would make me happy in a long-term relationship. And I wasn’t exhaustively vetting each potential date before going out with him.

I needed a comprehensive list.

“Are you there?” Hilary said, interrupting my thoughts.

“Hey, I’ll talk to you later,” I replied, taking another drag from my cigarette.

“Good. Just go to sleep. When you wake up tomorrow this will all be behind you,” she said. “Ooh ... Eric is just about to start the second course.”

I gulped down the rest of the wine in my plastic mug and then ran back inside to my kitchen table. I grabbed a legal pad and a handful of Hi-Tec-C pens, my trusted companions in Japan. Each was a bright color with a .25-millimeter ultrafine tip. I picked up the remaining book of matches and bottle of wine and went back outside. I had another two hours of summer sunlight and, at this point, nothing to lose.

I sat down at my patio table, arranging the notebook and pens in front of me. I poured another mug full of wine, lit a cigarette, and inhaled deeply. Suddenly, everything made perfect sense. How could anyone possibly look for long-term relationship potential without specifying all of the necessary traits in that person? Everyone—not just me—needed a list. I started to scribble down notes: 

WEBB-2-Smart

I stared at my notebook, flicking the ashes from my cigarette. Smart? Funny? That could be anyone, I thought. I started doodling on the bottom corner of the page, drawing three-dimensional cubes, when I saw some writing a few pages deeper in the legal pad. I flipped through and found an old grocery list from when I was still living with Henry: 

WEBB-3-produce

There was a logic to my grocery list. I always started in the produce aisle, so I began by listing the precise type of vegetable or fruit I needed, along with the variety. A tomato wasn’t just a tomato—there were dozens of options. Thinking about it now, I realized that I’d probably spent more time thinking through what to buy at the grocery store than determining what, exactly, I desired in a husband.

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