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.

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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.