What It’s Like Writing Pickup Lines for the Rich Dudes Who Outsource Their Dating Profiles

Turns out flirting with women your mom's age is a decent side-gig for students.

by Sarah Berman
Sep 18 2016, 3:05pm

Not Jim from Oklahoma. Photo by William Iven

This article originally appeared on VICE Canada

Some people are really, really good at online dating. Like, they can juggle over a dozen conversations at a time, sideline gross predatory shit, and get total strangers to like them enough to meet in public. Sometimes I think this is an unnerving, near sociopathic skill, but that might just be my outsider's perspective from being in a relationship older than Tinder.

What I've never once thought, though, was that this could be an employable skill—something that you could put on your resume and get paid for. It turns out sizable companies with account managers and writers and analytics departments exist to harness this (still potentially sociopathic) talent. I know this because I recently met up with Samantha, a 21-year-old student who recently worked this job. And while she assured me you can't get rich flirting with women older than your mom, she described it as a surprisingly decent side gig. I asked her a bunch of questions to figure out what makes this cottage industry tick.

VICE: So how did you get started on this?
Samantha: Applying was a lot more complicated than I thought it would be. It was quite a long set of tests. First you had to jump into a hypothetical message back-and-forth and try to get the date. In one of them you had to look at this guy's entire excerpt from a two-hour interview, and had to build a profile based on it, say things in a cheesy "charming" kind of way. And you had to draft pickup lines that you would use on somebody in a first hypothetical Tinder message, for example.

Was "there she is" one of them? Sam Biddle at Gawker memorably tested that one out.
That's not bad, actually [laughs]. They would test out these messages, sending them out to so, so many women. There are people who their whole job is to send first messages to women on these sites. Some of it is really basic, conversational, others get pretty pervy, grotesque. My job would be to jump in at the moment when the woman replies.

What's the best way to get these dudes dates?
It's a numbers game, you're talking to 20 women at a time for each client. It could be more than that. It takes an average of five to eight messages to get a number. You need to build a rapport before you can say "let's take this offline." So much research had gone into it, which surprised me. They had hundreds of spreadsheets of how different responses were taken. A lot of it is almost just exploratory to see what works and what doesn't. They recommended different pickup methods depending on how old the subject is. For example, deprecating humor works on younger women, but on older women, they say classic humor or straight to-the-point compliments work better... I guess what I read in the guides is they think younger women are stupid.

Gross. Were there many other women writers?
It was just a handful of women. They mostly want men writing for men because the ideal voice is a bit dominant, you have to be a bit deprecating.

Like straight-up negging women?
Yeah. There are some lines they suggest you use, like "Even in your worst photo, you still look pretty." Something really bad. "That shirt makes you look less pale," or "you look pretty good for a brunette." You would also want to make high-value statements about yourself. Say a woman would mention liking going to the beach, and then you'd say, like "Oh, I have a cabin in Bora Bora," something like that. Or "I have property overseas," [laughs]. "It's fabulous, if you like sand."

Wow. That is extremely corny.
They liked cheesy, painting-a-picture-type language. Trainers would tell us: don't just ask a question, give options. Say something like, "You're on your way to a vacation with your best friend, a free trip anywhere in the world, would you, a) go to a cabin in the Alps, ski all day, and sip hot cocoa at night; b) a beach hut in Tahiti—the only thing you need to pack is your favorite pair of flip flops..." That's probably almost verbatim one of the scripts they gave us. The funniest part was pretending you were this "charming" person.

Did you have to be in contact with these dudes you were ghostwriting for?
No, which I think is really lucky. Account managers would deal with all the clients and take in all the interviews and photos. We would get handed these interview transcripts where they describe their entire life up until that point—where they lived, what they did in school, what they do for work, their love life, everywhere they've vacationed, everywhere they want to vacation, their kids, their hopes, their dreams. Just everything. Even their favorite spots to go in the city. You would get a snapshot of everything you would want to tell another person. Then they would usually tell them to go out and get professional photos done. One of my favourite parts of the job was actually rating the photos. They would narrow it down to 20 or so, and we would rank them.

What did they look like?
They mostly look lonely and bumbling. A lot of them have been divorced already, and they just don't know what to do with themselves. Just so desperate and awkward and tragic. There was this ex-jock looking guy, he had professional photos taken, always with a hat on. One of them he was standing in a field with a backwards hat, polo shirt and little shorts, and there was just a chair in the middle of the field, and he was standing behind the chair with his hands on the back, just leaning in.

Like, 'this could be you' chair lean?
Yeah, this really weird invitational chair in the middle of a field, it was horrible.

Do most of these guys skew upper class?
I would say so, because the packages were really expensive. I think their target market is really rich older men who just don't have time to online date. So they hire 20-something women to do for them. But you also get the occasional mall security guard who just wants to find someone who likes anime as much as he does.

Did you ever feel personally invested in "dating" these women?
I wouldn't say I was personally invested in the women, they were a lot older than me. There would be times I'm like Christ, she's divorced, she has kids, I don't want to say that to her. I did get attached to winning, you really want to succeed and make commission. I think some people I worked with took some joy in finding people matches, but I didn't really care much about that. I was really detached—it was just entertaining for me. I feel like calling it matchmaking is sleazy in a way—it's shitty for that other person who thinks they're talking to a potential next boyfriend or husband who is so "charming" online, but actually it's a different person in a different city or country or gender, that's getting paid to message you. I feel like it could be a new-age rom-com.

Definite rom-com potential. Like an updated You Got Mail, where the profile manager falls in love.
Yeah, and they're trying to break through, maybe leaving some clues.

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Sarah Berman
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