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, Match.com, 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 Match.com 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?”

Untitled-1

“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.

“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.

If I was really making a Mary Poppins husband list, I ought to be as honest and detailed as possible. I needed to get much more granular.

What did I really want? In the movie, the list was torn up by the children’s father and sucked up into the chimney. What if I was able to magically create the man of my dreams? I didn’t have a chimney. But why risk a half-assed husband? I would have to list every single possible trait I could imagine.

1. Smart. He has to be a little smarter than me, and outwit me some of the time. He should have the kind of mind that hears something once and remembers it forever.

2. Funny. Someone with an acerbic, intellectual wit: Larry David created and writes Curb Your Enthusiasm, and along with Jerry Seinfeld also co-created the Seinfeld TV series, launching a whole new genre of observational comedy. Woody Allen: He used to write extensively for The New Yorker in the ’60s, critiquing popular culture through the lens of Archimedes or Freud. Judd Apatow: His Anchorman was hilarious because it was so true. So your basic pantheon of Jewish comedians. Plus Steve Martin, whose New Yorker essays and novellas are wry and clever. Steve Martin and the Jews. That’s what I want.

3. Jew ... ish. I need someone who was raised in a Jewish household. He should know what’s kosher and what’s not, what all the holidays are, the lore, and the history. He should know how to survive long shul services on nothing more than a few hard candies from his bubbie’s purse and a promise that if he will just sit still for five minutes, everyone can stop for ice cream on the way home. He has to understand all the inside jokes and have the same set of shared experiences. But he can’t be religious at all. It will be too difficult for me to fake a belief in God. If we don’t have exactly the same point of view on religion, it will absolutely cause problems during marriage. I know it may be a rare breed, but he must be a cultural, emotional, linguistic, intellectual, gastronomic, nonreligious Jew.

4. Not short. Between 5-foot-10 and 6-foot-2. Any shorter and I won’t be able to wear heels. Any taller and we won’t be able to snuggle in bed.

I felt my cheeks and the skin on my throat starting to burn. Could I be this picky? A man can’t help his height. Maybe there’s a guy on JDate right now who has the perfect sense of humor and dizzying intellect, just in a smaller package. I’m not exactly petite and thin myself. Was it fair to be this demanding?

Henry was very attractive. I was smitten the moment he turned around at the airport and answered me in English. He was funny, outgoing, and smart. But we were the same height, and deep down, that had always bothered me a bit. I liked the idea of being physically submissive in a relationship, when the timing and mood were both right. I wanted someone to overpower me, who could wrap his entire body around me in a hug but who could also throw me down on the bed and ravish me. I was too tall for Henry to throw me anywhere. Someone who’s smaller may be wonderful, but in my case he will never make me feel like he’s in control.

Fuck it, I thought. If I’m making a fucking list, I’m making a fucking list! I took another drink of wine out of my coffee mug and continued.

5. Body hair: Yes on arms, legs, chest. But not too much. No hairless balls or egregious manscaping. Since when did American society decide that a man’s hotness is achieved through aggressive chest waxing? Or “boyzilians?” If it was the 1600s and there were uncontrolled lice breakouts or other diseases in the village, fine. I can see getting rid of body hair. But I live in a city and I want a masculine-looking man. I know there’s a theory that getting rid of hair makes a guy’s penis look bigger, but in reality it makes him look like a prepubescent little boy. Unfortunately, I’d seen one up close. What woman wants to have sex with a giant-little-boy-man-penis?

6. Head hair: Curly and dark. As a teenager, I’d spent multiple summers at Olin-Sang-Ruby, a Jewish overnight camp in Wisconsin. Every year, there was a delegation from Israel, and invariably they were all cute. My first kiss was with one of those olive-complected, curly-haired Israelis, and I’ve been attracted to that type ever since. But I also have another, less obvious type: stylish balding with high-end glasses. (No male-pattern balding in the back. No surprise balding that’s obscured with a baseball or other hat.) On TV and movies, they tended to play the supersmart, if slightly nebbishy, lawyers and doctors: Evan Handler, Jeffrey Tambor, Stanley Tucci. My astronomy professor in college looked just like Stanley Tucci. He was from the East Coast, had a bit of an accent, and wore glasses. He was wickedly smart, had a dark sense of humor, and was incredibly sexy.

7. Likes musicals. Likes selected musicals: Chess, Evita. Not Cats. Must not like Cats! Yes. There, I’ve said it. I’m not going to listen to show tunes cranked up to a maximum decibel level like when I lived with Henry.

8. Must not be in debt. At this point in our lives, he should be done paying off loans and shouldn’t have massive credit card debt. Mortgage is acceptable.

9. Must make enough money to be comfortable and should have a sustainable income. He doesn’t need to be wealthy. But he should have a source of secure income and some kind of bank account. If he loses his job or can’t work, he should be able to float for at least a year. I don’t want to be in a situation where we’re living paycheck to paycheck.

10. Must not smoke. Must insist that I don’t smoke either. I need to stop my one smoke several-cigarettes-a-day habit, and that’s only going to happen if he is an ardent nonsmoker.

11. Must not do drugs. I tried to experiment in college, but the one time I smoked pot I felt nauseated and fell asleep on my roommate’s friend, who was visiting from somewhere in West Virginia. The whole process seemed like a waste. I certainly don’t want someone who is into drugs now.

12. Must have an actual career. Cannot be an aspiring writer/chef/artist/whatever. If he says he’s a doctor, he needs to produce actual ID on the spot. I can’t go through another date like the one with John, the fake orthopedic surgeon.

13. Career must be important but not all-consuming (like mine). He has to understand a sensible work-life balance, since I don’t. I need him to teach me how to cultivate hobbies and how to not work constantly.

14. Must understand how important my career is and be willing to support me in it. If I have to spend a Sunday working, or if a client needs me at their office for a few days, he must be able to give me space and should not feel threatened.

15. Age: between 30 and 36. I suppose there are 25-year-olds who are interesting, but they’re in a different place than I am now. Too much older than 36 will be a big gap. I need someone close to my own age, and if I’m being totally honest, I want someone who’s only one or two years older than me so we can make the same pop culture references.

16. Never married before. No crazed ex-girlfriends either. No children. No insane mother or other mother issues. And not fucking currently married!

17. Wants to have two kids with me. This is non-negotiable. I’m going to want to be pregnant within the next three years, so we may as well agree to this at the beginning.

18. Doesn’t drink all the time. Just occasionally. Doesn’t “need” a beer or a cocktail in order to eat dinner. I have friends who insist on only going to BYOB restaurants so they can bring their own wine. Other friends complain if a restaurant doesn’t offer a certain beer on tap. We’re there to eat, not get drunk.

19. Likes the outdoors. But only enough for a picnic or grilling in the backyard. Doesn’t want to spend the day golfing or reading on the beach. Isn’t compelled to do overnights at rustic campsites. Driving a car up and down a mountain range should count for “hiking.”

20. Likes dogs. Preferably not big, shedding, slobbery dogs. He should like smaller dogs, like beagles or dachshunds. Doesn’t necessarily want to own one right now.

21. Likes to watch TV, movies. Acceptable “good” TV/movies include: Cheers, Coupling (U.K. version only), Arrested Development, Curb Your Enthusiasm, Deadwood, Six Feet Under, and Seinfeld. He should also hate to watch sports. Especially golf.

22. Appreciates my quirks and neuroses. Should be both impressed and entertained that I took a color-coded binder full of spreadsheets to an introductory therapist session.

23. Challenges and stimulates me. Should have good, long discussions. We shouldn’t agree all the time, but we should be able to have amicable disagreements.

24. Has lots of integrity. Highly ethical. He should be competitive, but not someone who cheats to win. Clarifications: Driving 20 miles per hour over the speed limit may technically break the law, but I’d argue that many speed limits are set too low. Speeding = OK. Lying on a tax return or cheating on a wife is unethical. Tax fraud = Not OK.

25. Has a positive outlook on life. He should be in a good mood most of the time, seeing opportunities rather than obstacles. I don’t want any complainers.

26. Is mature ... is a grown-up. Doesn’t lose his mind if he doesn’t get his way. Henry often got upset when we didn’t do exactly what he wanted. He’d mope around or angrily go off on his own and do something else.

27. Likes computers and gadgets, like me. Interested to learn more.

28. Appreciates the beauty of a well-crafted spreadsheet.

29. Can fix anything. If not, is willing to tinker to figure out what the problem is. And if he can’t do that, then he should have someone on speed dial who can come and solve whatever the problem is. I have curly hair that constantly gets coiled around drains and plumbing. During the halcyon big-hair days of the ’90s, our college bathroom was a wreck. None of my roommates knew how to take apart a toilet or snake a drain. We’d let the water pile up in the shower until it neared our shins, and only then would we reluctantly make yet another call to the plumber.

30. Really appreciates and understands me. Knows my motivations without explanation.

31. Is genuinely able to crack me up. He should be inherently funny without having to make fun of other people. Like Jerry Seinfeld, he should make hilarious observations about the present situation.

32. Lightning-fast thinker. Witty. Brilliant, but not professorly. He should make me feel like I’m a few clicks behind him on the IQ scale.

33. Adventurous. Doesn’t want to sit still. He should be willing to take a day trip to go tour a historic house or hang out at a street festival or try a new restaurant.

34. Is willing to move, to not be stuck in one place forever. But he can’t want to drift. He should be in the process of establishing long-term roots.

35. Loves to really travel. Not cruise-ship travel. I want to visit Petra, Jordan, and walk through the ancient ruins. I want to bring him to visit my friends in northern Japan. I want us to re-enact my favorite scene from The English Patient, when Count Almásy and Katharine wander around the souks in Cairo.

36. Be from Chicago or willing to fly there often to see my family and to spend time with my mom.

37. Be able to advise me on matters of business and everything else. As a business owner and as a wife, I need to have a partner in life who can help advise me.

38. I have to think he’s smart enough and savvy enough to then take his advice. He should be right most of the time. (But he shouldn’t necessarily know it.)

39. Mac person preferred over PC person.

40. Be very good with money. Understand how it works. Make it work for us. Ideally, he should manage his books, and he should know how to make sound investments for the long term. I don’t want any petulant day traders or emotional investors. He should also be humble and have the good sense to never talk about money publicly.

41. Be willing to go out on romantic dates. Plan fun getaways, surprises.

42. Feel compelled to woo me. But in a restrained way. I don’t need my name on a billboard or skyscraper. He should pay deep attention to me, remembering the various details of the things I’ve told him. He should notice the little things, like if I’ve cut a few inches off my hair or that I prefer dark-roasted coffee.

43. Likes jazz. Likes jazz only from the 1920s to the late 1940s. Growing up, we always listened to my dad’s record collection, which included Sidney Bechet, Cole Porter, Artie Shaw, Ella Fitzgerald, Benny Goodman, Billie Holiday, Django Reinhardt, and Stéphane Grappelli. Also acceptable (but later): Vince Guaraldi.

44. Like classic movies: Casablanca, The Philadelphia Story, anything with Peter Sellers.

45. Be an excellent trivia partner.

46. Enjoys Jeopardy! He shouldn’t make fun of me if I don’t know the answer to a question. Henry used to say “nice job” with this horribly condescending tone, like he was shocked when I answered a question he didn’t know.

47. Be a reader. Own books. Preferably stuff from Fitzgerald, Hemingway, Heinlein. Also Michael Lewis, Steve Martin. He should have a bookshelf overflowing with an eclectic mix of well-worn Fodor’s and Lonely Planet travel guides.

48. Either like to dance or be willing to dance with me. Looking like a complete ass while dancing is totally acceptable.

49. Be willing to listen to George Michael and never make fun of me for loving his music. Endure me singing along to the Listen Without Prejudice album often. Attend George Michael concerts when asked.

50. Dress well, in a way that I can appreciate. Nice shirts; well-fitted pants and suits; unusual, quirky socks. He should care about his appearance and strive to look good for me. Note: no athletic team shirts or jerseys.

51. Be of medium build. Not fat, not skinny.

52. Must weigh at least 20 pounds more than me at all times, whatever I happen to weigh at that moment.

53. Should not be supermuscular. I don’t want a former athlete who’s trying to reclaim his 18-year-old body. No protein shakes or other nutritional supplements should ever make an appearance.

54. Must be very accomplished. Should be on boards and seen as a leader in his industry. He should be a humble polymath.

55. Be secure and quietly confident. But not arrogant.

56. Should not succumb to jealousy of me, of colleagues, of family members.

57. Genuinely like and appreciate my giant, loud Jewish family.

58. Likes cities, hates suburbs. I want to live in a place full of excitement, culture, and opportunities. Ideally, we’ll walk to the market together for groceries and try a new restaurant once a week. He should abhor chain restaurants and the McMansions of suburbia.

59. Must share most of my interests: touring historic homes, playing with new technologies, attending seminars and conferences. Of course, he should also share my non-interests and have apathy toward long road trips, mall shopping, wine culture, hanging out in bars listening to local bands.

60. Is willing to participate in or try some of my activities: learning about cooking and cuisine, going to museums, seeing new places, etc.

61. Shouldn’t get angry. He should never feel compelled to punch a hole in the wall. Henry had a really bad temper and once got so angry at me that he slammed his fist into the wall about 6 inches away from my face.

62. No history of cheating. Not on a test, not in a game of poker, and certainly not on a former girlfriend.

63. Be totally devoted to me. He must listen well, pay attention, and love me intensely.

64. Be physically affectionate but not overbearing. I want him to hold my hand in public, not deep throat me at Sunday brunch.

65. Be adventurous in bed. He should be willing to try new things, new places, new techniques, without my prompting. He should be confident enough to pull off whatever that sexual adventure is.

66. Be very, very, very good in bed. I cannot stress this enough. He has to be amazing—so amazing that I’ll feel sheepish talking about him to any of my friends.

67. Must be very friendly (but not in a fake way) to waitstaff. He should be like Jay on our date, before he became a lecherous asshole.

68. Should be easygoing, adaptable. If plans don’t work out his way, he should be able to move on without whatever it was ruining his entire day.

69. Must get along well with Hilary. Non-negotiable!

70. Must be unflappably dependable. He should never forget dates and can’t flake out on our plans. If he says something, he should mean it and follow through.

71. Must have an excellent vocabulary. He should feel comfortable correcting me if I misuse a word.

72. Should never have the instinct to high-five me. No high-fiving allowed!

I sat back in my chair. I was no longer angry at Jay and lamenting my decision to go out with him. No, at this point I felt empowered, and proud of myself for being honest enough to develop such an impressive list of 72 data points. This Mary Poppins Husband List was exactly who I needed to make me happy. He was right there, detailed in black ink. None of the men JDate, Match, or eHarmony had introduced me to resembled anything like the man I’d just created with this list.

I lit another cigarette, celebrating my accomplishment. Then it dawned on me that I’d inadvertently created a small problem. What was I supposed to do with three pages of hand-scrawled notes? I needed to make sense of what I’d written. Reviewing my list, I noticed some duplication, so I’d need to fix some of what was there. I couldn’t really use the list as it was—I needed to codify the traits and characteristics.

In order to use it to judge future potential dates, I needed to prioritize the various data points. Was every one of the 72 traits I’d listed a deal breaker? Honestly, I could live without a husband as devoted to George Michael as I am. And it was probably OK if he wasn’t a classic-movie fanatic.

I decided that the list had to be sorted and tagged, using three frames of reference: traits in partners from previous serious relationships, traits demanded by my family, and traits I considered to be top priorities in order to please myself.

Thinking about Henry, I could see that there were some things that worked in our relationship. There were also plenty of issues that seemed to be problematic in other past relationships. For example, I wasn’t good at social drinking. My body seemed to transition from sober to drunk without warning, and as a result I didn’t like hanging out at bars. Sure, I was smoking as I made the list, but I didn’t want an occasional or social smoker. Instead, I wanted an avid nonsmoker who would force me to stop.

Was there a pattern to the men I’d dated previously? What were the common traits shared by men from my past relationships? I lit another cigarette.

Next to my legal pad were several Hi-Tec-C pens in different colors: red, green, blue, purple, and black. I decided to color-code the list for each set of traits, marking a small dot next to the list entry. I rolled the green pen toward me and at the top of the paper wrote: “Traits in Partners From Previous Relationships.”

I thought about Henry and about all the other relationships I’d been in that lasted more than a few months. I marked a green dot next to each trait that was relevant:

  • Smart
  • Funny
  • Interesting
  • Between 5-foot-10 and 6-foot-2

That’s it? That can’t be right, I thought.

I scanned the list again, objectively evaluating each trait and holding my green pen close to the paper. I’d just made a comprehensive list of everything I demanded in a husband, and of everyone I’d dated—even casually—there were only four traits that previous partners had? No wonder those relationships didn’t work out. I put my plastic mug back up to my lips and tilted my head back as far as I could while still focusing on the paper, but there was nothing left. I licked the rim a bit. The wine, Chateau LaFou–something-or-other, wasn’t very good, but the taste was starting to grow on me. I put the mug down on the table, reached for the bottle, and poured.

I rolled the blue pen toward me and wrote “Traits Demanded by My Family” at the top. Then I combed through the list, marking blue dots next to each one of the traits that qualified:

  • Smart
  • Jewish
  • Must not smoke
  • Must have actual career
  • Wants two kids
  • Has a positive outlook on life
  • Is mature, a grown-up
  • Lightning-fast thinker
  • Be from Chicago or willing to relocate there
  • Be very good with money
  • Must genuinely like and appreciate my family
  • Shouldn’t get angry
  • No history of cheating
  • Be totally devoted to me

This, of course, made sense. My parents, sister, grandparents, aunts, and uncles all wanted me to find someone who would treat me well, who would keep me interested, and who would fit into our existing family structure. They wanted me to be in the kind of relationship where I became a better version of myself.

Now, I thought about what was crucially important to me. What were the traits I’d need in a husband in order to make me truly happy? I brought the red pen up to the paper, at the top wrote, “What I Need To Make Me Happy,” and judiciously awarded red dots:

  • Smart
  • Jew ... ish
  • Career is important
  • Wants two kids
  • Challenges and stimulates me
  • Is genuinely able to crack me up
  • Be very good with money
  • Must genuinely like and appreciate my family
  • No history of cheating
  • Be very, very, very good in bed

Now that it was dark outside, I had to use the light from my computer to review all of my markups. My list was now covered in different colors. It made basic sense, but a spreadsheet would help me to visualize what was really important. As I pushed my chair back, it rumbled against the wood of the patio deck. I knocked against the table a bit as I stood up. I was dizzy, and the backs of my legs tingled. I checked the time on my mobile phone. It was 10 p.m.? How had three hours passed?

I brought my bag back outside and arranged my MacBook on the table next to my list. I opened up a basic spreadsheet and entered all of the traits from each color:

WEBB-7-Traits

Using the red list as a base, I decided to narrow the pool down to a prioritized list of 10 deal breakers. Since no drugs and no smoking should both be assumed, I disqualified them from consideration. Ten seemed like a good round number. I didn’t feel like I was being too greedy, and I was focusing on the things that mattered most.

I started a new spreadsheet, typing my 10 deal breakers in priority order in one column. In the next column, I gave each a score to weigh each trait: 10 = highest, 1 = lowest: 

WEBB-8-Top-tier

I took a sip of wine from my coffee mug and thought about what was on my screen. I’d just ranked what traits in an ideal husband were most important to me and to the people in my life. These 10 deal breakers made perfect sense, but there were other data points on my list that I knew were also significant. Ten was just an arbitrary number, I figured. So why not create a second tier of almost-as-important traits, and change the weighting system? Deal-breaker traits would receive a distribution of the 90th percentile of points available out of 100. Then I could give the second-tier traits much less weight by allocating fewer than 50 points per category:

WEBB-9-Large-trait

It would be highly unlikely that someone who scored a maximum number of points in the second-tier category would not also score at least several of the more heavily weighted deal-breaker traits. Glen would have scored a 50 if I was feeling generous, and I would have given Jim about 150 pre-date.

Looking at my list now, 150 points shouldn’t have qualified Jim for a date. Karaoke night with Glen should never have been an option. What was a good number? Doing some quick math, I decided that from here forward, anyone I’d consider going out with would have to score an initial 700 points. He could get extra credit in any category up to 10 points too. This would ensure that I would eliminate bad dates before I had the chance to go out on them. In order to score a potential date accurately, I’d have to use email or instant message and also talk to him on the phone long enough to determine whether he’d met the 700-point threshold.

And then, after the first few dates, I would force myself to re-score him. In order to enter into a relationship—a semi-serious one, even—he’d have to score a minimum of 1,000 points. That would mean he’d met at least seven of the top-tier traits and most of the second-tier list.

I resolved to honor my list and scoring system from that point forward. I grabbed my phone and called Hilary. I knew it was late. I didn’t care.

“Hello?” she said. I expected her to be at home in bed, but she was still at the dinner party. I could hear just a few men talking, laughing a little.

“I did it,” I said, nearly shouting. “I made the list!”

“What list?” Hilary asked.

“The Mary Poppins husband list you told me to make!”

“No ... ,” she started.

I started rattling off each data point. “One ... smart. Because, you know, he has to be brilliant. Two ... funny. He has to completely crack me up ...”

“Wait a minute,” she sighed, exasperated. “Let me get somewhere quiet.” During the short pause, I imagined her excitedly scurrying to the bathroom again, as giddy as I was about what I’d just created. In reality, she was probably rolling her eyes at her friends and making that pointed-finger crazy gesture at her head. “Oh, it’s Hilary’s poor deranged sister again,” fabulous Eric was saying from his charming black leather sofa.

“OK,” she said. “I’m in the bathroom. Go ahead.”

I read Hilary the entire list, all the way down to number 72. Then I explained how I’d prioritized and color-coded it, assigning numerical values to each trait. I told her that I would refuse to go out with someone until he reached a minimum score of 700, and how any future husband had to score at least 1,000 points.

“It’s a flawless plan!” I concluded, waiting for a response. A few seconds went by. “Are you still there?”

“Amy, you need to destroy that list,” Hilary said. “Or fold it up and put it somewhere where no one will find it.”

“But don’t you see the beauty in what we did?”

We didn’t make a list with 72 different things you’re demanding in a husband,” she reminded me. “I was just trying to make you feel better.”

“But the reason I’m going on all these bad dates is precisely because I didn’t have a detailed list of what I need to make me happy,” I said. “It all makes perfect, logical sense now. It’s just math. I can see it!”

“There’s no way you’re going to find someone who scores—what was it?—like 2,000 points on your scale. This is just going to make things harder for you,” she said. “Trying to find a husband who fits the exact list of what you want is going to be like looking for a needle in a haystack. You’re never going to find him.”

“That’s where you’re wrong,” I said. “It’s dead easy to find the needle. You hack the haystack. Knock it over, scan it with a metal detector, find your needle.”

TODAY IN SLATE

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