Amy Webb’s Data, A Love Story: Using algorithms and charts to game online dating.

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

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.

Author Amy Webb.
Author Amy Webb.

Courtesy of the author.

This is an excerpt from Amy Webb’s Data. A Love Story: How I Gamed Online Dating To Meet My Match, which comes out today.

It was now July, a few weeks since my date with Jim, the weed smoker who refused to split our dinner bill. I knew matching algorithms weren’t perfect, but I kept dating and decided not to cancel my memberships with eHarmony,, and JDate. The majority of dates I’d been going on weren’t horrible, they just weren’t great. I was an optimist rooted in math and logic. I knew that if I spent enough time searching through each site and going out with a large enough group of men, I could increase the probability of my finding the right one. And besides, even if I canceled, I knew how Internet marketing worked. All three services would continue to email me new profiles every day.

Subject: Hot Match!

Message: We have a new match for you! LegalTruth20 is 34 and lives just a few miles away from you! You haven’t logged in recently. Don’t keep LegalTruth20 waiting!

I was sitting at my desk at work when sent me a similar reminder message, this time highlighting MenchTastic, and his profile immediately grabbed my attention. He was 33, was a nonsmoker, and said explicitly that he wanted kids. He was also a journalist covering the city hall beat for one of the local newspapers. I was intrigued enough to click through and read the rest of his profile.


In his About Me section, MenchTastic wrote, “I’m a journalist, which sometimes means long hours at work but always means I have fantastic stories to tell.” Looking at his profile, I thought that I might know his byline. Even so, we shared enough similarities in our personal and professional lives that it felt as if, even as strangers, we’d been a part of each other’s social circles for many years.

I moused over his photo gallery and started clicking through. He had thick, dark curly hair and wore modern horn-rimmed glasses. In one picture, he was wearing white slacks (linen maybe?) and a navy long-sleeve shirt. He looked serene and content, standing with a very tan, old sailor behind the wheel of a large yacht. In another shot, he was sitting at his desk at work, surrounded by stacks of newspapers, file folders, and paper. On his desk were a coffee mug and a pile of reporter’s notebooks along with two giant computer monitors. Dozens of press-pass badges were hanging on his cubicle. In the next photo, he was out at an event, dressed in a black fitted shirt and dark slacks. He was slender, tan, and seriously attractive.

As I clicked back to his profile, an instant message window popped up on my screen:

MenchTastic: Hey there

“Shit!” I said aloud. He’s caught me looking at his profile. What do I say?

Yozora: Hi ...

I waited to see what he’d write back.

MenchTastic: I don’t have a lot of time to chat now. On deadline at work. What do you think about getting drinks sometime this weekend? Or tonight? Technically the weekend starts in a few hours. ... Are you free?

I immediately heard Hilary’s voice in my ear. “You can’t go out with him tonight! You can’t make yourself that available.” But he’s so good-looking. And he’s a journalist. And he’s asking me out. Aren’t I supposed to date everyone right now? Cast a wide net and see what I catch?

Yozora: Sure. Want to meet at Longshots on Fairmount Avenue after work?

As soon as I hit Send, I felt a strong tingle in my stomach. Then instant regret. Did I just ask him out by accident? Shit! I bet I just came on too strong. I should have ...

MenchTastic: 6pm tonight. I’ll meet you there?

Yozora: Sold.

I rifled through the piles of paper on my own desk looking for my mobile phone. Where did I put it? Not under the file folders. ... There, underneath my laptop. I dialed Hilary and waited for her to answer.

“So I met this guy on Match,” I said. “He’s a journalist. He sort of looks like Jeff Goldblum, but the Independence Day Jeff Goldblum. Not modern-day Jeff Goldblum. He seems really smart. He looks smart.”

“Yes, I can talk even though I’m at work and this isn’t an emergency,” Hilary said back.

“Sorry. Can you talk? Great. So anyhow, he seems normal,” I continued.

Hilary sighed heavily. “What does he do again?”

“Journalist,” I said, taking a big gulp of coffee. “I actually think that I know who he is already. I’m pretty sure he’s a friend of a friend of Juliet’s.”

“Do you think that’s a good idea?” she asked. “Won’t you both be too competitive, trying to get scoops or whatever? We all know that you’ll assume he isn’t smart enough for you.”

“Very funny,” I said. “He wants to go out tonight.”

“Uh, you can’t go out with him tonight. It’s Friday night and you’re available? He’s going to think you’re desperate,” she said.

“Why can’t he just think that I happen to have some free time on the night that he happened to ask me out?” I said, taking another drink of coffee.

“What are you going to wear?” she asked.

“I was planning on going straight from a client meeting, so black pants—”

“You can’t do that,” Hilary interrupted. “If you like him, you need to go shopping. Your black pants and black or gray top or whatever you’re wearing isn’t good for a first date. Jeff Goldblum isn’t going to date someone who wears what you wear to work.”

“Well, I don’t have time to go shopping,” I said.

“That’s another reason you shouldn’t go out with him tonight,” she said. “Listen, I’ve gotta go. I’m busy at work.”

My date with MenchTastic kept me preoccupied the rest of the day. I sat through a client meeting discussing the usability of a website, and all I could think about was his photo gallery. Where was that boat? Did he know how to sail? I bet he has sexy hands—strong, veiny even, but soft. I looked at my watch more often than I should have, waiting for the meeting to end. We finally wrapped up our discussion, but without enough time to head home first, I went straight to Longshots and decided to wait at the bar for him.

I ordered a club soda with a twist of lime, which looked like my usual first-date drink but contained none of the potentially dangerous alcohol. MenchTastic would likely order a drink once he got here, and since I actually liked him I didn’t want to get accidentally drunk at the very beginning of the date. Since it could happen so quickly, I usually didn’t realize I was drunk until something bad had already happened. It could take just one strong drink for accidentally drunk and unwittingly aggressive Amy to rear her ugly head, and the bartenders at Longshots were too unpredictable to entrust with this very important first meeting.

Drink in hand, I commandeered my usual position at Longshots: the overstuffed leather sofa in the back corner. It was dim but not too dark, and it was the one place in the bar that didn’t cast the kind of bad shadows that could add a week of sleepless nights plus another 20 years to my face. I threw my gigantic bag, packed with my laptop and dating data, next to me as I sat down and sunk into the cushion.

By now, the waitstaff and bartenders knew me by name. For the past few months, I’d been having drinks at Longshots with different men at least twice a week. I never stayed more than an hour and always made at least two trips to the bathroom. They must have suspected me of something, though they weren’t quite sure of what. Was I a drug dealer? A prostitute for men with a haggard-office-lady fetish? What was in that huge bag of mine?

Just as I was taking a sip from my glass, I saw MenchTastic walk through the door. He was just under 6 feet tall and solid but not overweight. Even in the dim lighting, I could see that his olive skin had a healthy glow, as if he’d just been to the beach. With his black pants, dark blue button-down shirt, black overcoat, and messenger bag slung across his chest, he looked like he’d walked right out of a J. Crew catalog. So far, his profile was accurate. A good sign. He seemed to recognize me instantly too and walked straight toward me.

“Hey! Thanks for meeting me tonight,” he started. “I’m Jay.”

“Hey—I’m Amy,” I said, smiling back at him.

Jay removed the messenger bag from his shoulder in one smooth movement and put it, along with his coat, next to my gigantic bag on the couch. Our conversation flowed easily. He’d been on a deadline that day, working on a story about how a city councilwoman may have misappropriated campaign money for her own personal expenses. He’d managed to get a coveted interview with one of the investigators, a primary source, which meant that he’d be able to go through documents together with the councilwoman and have her explain what the audit showed. I mentioned that long ago when I was a reporter, I’d used a pocket scanner I bought in Japan to make copies of documents. He’d been using a digital camera to take photos but thought the scanner was a much smarter idea.

As we talked, I noticed our voices overlapping and moving in cadence together. We weren’t quite finishing each other’s sentences, but I mirrored his enthusiasm and found myself thinking faster and grinning more. I’d moved in closer to him and hadn’t once thought about my laptop or email rating system. I was too eager to hear what he would say next.

The waiter came by and asked if Jay wanted to order a drink. Longshots offered an extensive menu with pages of specialty drinks and, in the back, several more pages of coffee roasts and flavors. Jay said he wanted coffee. He’d just filed his story, and he wanted to be alert in case the copy desk called with questions. “I’m looking for something that has a rich flavor, maybe even nutty or chocolaty,” he said. “What do you recommend?”

Our waiter seemed genuinely delighted to share his knowledge. He explained that he helps to select which small coffee-bean purveyors Longshots uses.

“The El Salvador Verro de los Ranos Peaberry is delicious. And it’s sustainable, which is awesome,” he said. “The fair-trade Guatemalan Huehuetenango—”

“Wait. Say that again?” Jay asked, smiling.

“I know, it’s a mouthful, right?” the waiter said. “Hue-hue-ten-an-go. It’s on the spicy side. For that, I’d recommend double espresso, without any sugar if you’re able. I can serve it with a few twists of orange peel to bring out the citrus notes.”

“Well, I don’t think I have a choice, right?” Jay joked. “Hue-hue-ten-an-go, with peel!”

What a shockingly different experience from my ill-fated date with MrJim1971, who wanted to be the know-it-all expert on food and wine during our insanely expensive meal. He wasn’t interested in taking recommendations or even in asking my opinion. I loved how, in contrast, Jay was so genuinely, naturally inquisitive. At least at Longshots, he wasn’t making assumptions. He was asking thoughtful questions and paying attention to the answers. Curiosity was one of the hallmarks of a good journalist.

As we waited for the coffee, our conversation began to wander from city hall to China. He’d been fascinated with Asian culture and was hoping to travel to the outer edges of the Great Wall. I told him that I’d once been to Dalian, a small city in the northeast. I was on a reporting trip, trying to learn about how China’s hyper-productive manufacturing scene was affecting nearby countries. One day, it was so brutally cold that I wandered into a tea shop to warm up. The owner knew English and didn’t have a chance to practice it often, so he was thrilled to see me. We spent the next two hours tasting every one of the 38 teas he had in his shop. He explained that he sold 38 teas because eight was a lucky number in Chinese, and the three in front of it meant “triple prosperity.”

And then Jay’s phone rang. He looked down at the screen and rolled his eyes. Cupping his hand over the receiver, he whispered, “I’m really sorry. I need to take this. Two minutes?” he said, holding up two fingers. I rolled my eyes back at him to commiserate as he walked back toward the bathrooms.

I knew what it was like to get those calls and to be available at all hours. Journalists, especially those on a daily desk, were never really off the clock. Copy editors would want clarification on the spelling of a name, or to say they’d cut several key paragraphs out of a story because there wasn’t enough space. It was an infuriating but necessary part of the job. If Jay’s story was as controversial as he’d intimated, this would be only the first of many calls he’d receive throughout the night. I understood completely.

Jay walked back toward me, phone in hand, the corners of that warm smile not quite as outstretched as they were earlier. He pushed our bags aside and this time sat down right next to me, propping his elbow up on the back of the sofa.

“OK, sorry about that. So tell me more about Japan,” he started. Had I ever eaten puffer fish? Was I worried about getting poisoned? What about Japanese onsen—the hot springs? Were the co-ed baths awkward for me?

It was a subtle opening I’d been waiting for, an opportunity to be flirty without flirting. Yes, I loved visiting hot springs. Most were no longer co-ed, but even so, I wasn’t bashful or embarrassed. Communal bathing was a deeply rooted part of Japanese culture. It was a matter of understanding how to bathe properly. In a large room, I’d undress completely and neatly stack all of my clothes into one of the wicker baskets provided at the onsen. Then I’d walk naked toward a washing area. There were little stools, mirrors, and showers positioned so that I could lather every area with soap while sitting down. Once completely clean, I’d go over to one of the hot pools, dip my toes in first, and inch the rest of my body in as I acclimated to the heat, I explained.

“I’m sure all of the men stared at you,” Jay said. “What was that like?”

“I don’t know that they were staring ... ,” I said. I could feel my cheeks growing warm.

“You’re beautiful,” he said. “I’d stare. Plus, you have American breasts!” he laughed, putting his hand on my knee in a way that wasn’t forced. Suddenly, I had a strange inclination to high-five him.

Jay’s phone lit up again. This time, it was a text message. I shot him a knowing glance. The copy desk, no doubt, had yet another question.

“Ugh,” Jay said. “Sorry, I just need to make a quick call. Do you mind?”