The Confessions of a Rich Asshole’s Former Online Dating Surrogate

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All names, aliases, and identifying details have been changed.

The address that emailed me,, sounded more like a newsletter listing Manhattan parties and Brooklyn festivals than a man searching for love. It included more of my own words than his, a smart move.


You may recall writing the response below to an ad for an online dating surrogate. Are you still up for the job? Your response was funny. I think you could help. Josh

Dear Successful Entrepreneur,

I would be delighted to be your online dating surrogate. I have piles of online dating experience, a job in a writing-related industry, and a long and storied history of judging other women. If my fully-packed friend-wedding calendar is any indication, I have great taste in ladies – but if my fully-packed Saturday-night-bar calendar is the measure, I also have great taste in super fun gals.

Let’s find you love, boy.

It had been three months since I had applied for the job, and in the meantime I had forgotten that an “online dating surrogate” was a thing that could exist. I hadn’t been looking for a side gig. Instead, I’d come across a post on Betabeat describing the Craigslist post and calling Josh the “World’s Biggest Douchebag.” I didn’t disagree — in his ad, he described himself a “successful entrepreneur” looking for a “pretty, thin, educated female in her 20s or 30s,” to help him comb through dating profiles and approach women, as he was simply too busy. Why his middlewoman needed to be attractive and svelte was unclear, but the money was easy and the job was an irresistible conversation piece. Just like responding to an ad on OkCupid, I chose a picture of myself fifteen pounds lighter and put my best foot forward. My enthusiasm for the job had waned in the intervening months, but my enthusiasm for a quick buck is a reliable constant. I replied, asking for his parameters.

Josh’s standards for a potential date were strict, but more difficult to argue with than I imagined. I cringed at his racial requirements (whites only, like a ’50s water fountain) and attempts to put a weight limit on prospective matches. Basically he was looking for a nonsmoking Jewish brunette in her early to mid-30s with a college education, graduate degrees preferred. This struck me as a fairly respectable ask for a man trolling for “NYC events.”

I’ve been dumped for pre-existing conditions once or twice, and had to admit that people need to be allowed to have their preferences up front. I didn’t want to waste the time of a Japanese single mother or a 24-year-old Latina smoker or a voluptuous blonde follower of Christ with a GED. My job would be simple to start: I would use my own unpaid account to scout for women, and five times a week I would send a PDF containing 10 photos and usernames to Josh. In return, he would give me precious money, $100 a week.

I crafted a fake profile full of double-entendres and general asshattery, as a tribute to the Josh I’d never seen or spoken to in real life. JackAndCokeUWS was blonde, athletic, never married, and a cigar aficionado. He had grown up in New Canaan, was interested in owning exotic pets, and listed Joe Rogan, Olivia Munn and fantasy football among his favorite things.  He was looking for “a real guy’s girl… a cook in the kitchen, bro in the bleachers, and freak in the sheets.” For his face, I considered the Craigslist Killer or Scott Disick, but used Tucker Max. The profile was an exercise in personal amusement, but I also pretended it offset my own emails, one of which I had signed “let the judging begin!” But Josh was the jerk, right? And I would show him, by making this profile and never showing it to him.

Later, when I saw how popular JackAndCokeUWS was with a certain type of woman, I realized that there was no reason to mold my avatar in Josh’s imagined image. Women wrote to JackAndCokeUWS in droves; my paywall undulated with unread messages and, presumably, the silent screams of the lovelorn. Instead of this cruel chick magnet I could have created a shy boy, or a prototypical neckbeard, or just a blank profile with nothing for the susceptible women of the Internet to project their expectations upon.

On Match, I entered Josh’s criteria into the search field. Almost all of the parameters were accounted for in the algorithm, so I only needed to evaluate pictures, with a cursory profile glance to make sure there was at least a grasp of basic grammar. The first day I browsed for hours, marveling at how accomplished, pretty and serene the 30-something brunettes of New York appeared to be: their careers, their international vacations, their shiny hair. I found a formidable army of women and stored them away.

A moral issue arose when I started sending packets to Josh. How would I refer to the contents of the email, as PDFs or as women? On my computer I had saved their photos in a folder titled “LAYYYYDIES,” because shout-y misspellings make things ironic. Now that I was presenting the women to Josh, their thumbnails and carefully chosen usernames, they felt real. I couldn’t continue to minimize them; I knew more about them than I knew about Josh. I had seen their pixelated little faces, and read the things they wanted a man to know about them, not just a list of their own demands. In the email that accompanied that first PDF, I referred to them as “nice ladies” and “impressive women” and raved about their beauty and intellect. I jokingly demanded to be his best man, gave unsolicited advice about the wink feature, and signed off as “Your Virtual Wingwoman.”

Josh said I had a good eye.


My PDFs were arranged strategically: pretty, pretty, less pretty, flattering photograph of a woman who violated the proposed weight statutes of the agreement, plain, gorgeous, pretty, plain, clear violation of terms, pretty. I wanted to get the most out of the women I had, to pad the results with women I knew to be nos and save the yeses for later so it would look like I was searching diligently every day, doing a good job, having a good eye. Was this woman a two slot, or a three? Did I have enough sixes, if sixes were proverbial 10s? Was I committing an act of psychic injustice against any woman in the four or nine slot, setting her up for a big zero?

I couldn’t pin down my feelings on Josh. His emails were short and business-like, sometimes acknowledging but never joining in on my jokes. He didn’t give much feedback, which I considered confounding. Once, when I asked, he informed me that some of the women I’d sent “just can’t squeeze into the slender category,” specifying which ones had tipped the scales out of her favor. I was indignant, but I had asked. I tried disliking him and it felt unearned. I tried liking him and I just didn’t. I plowed ahead.

Once, I found myself watching episodes of Criminal Minds as I browsed. The Behavioral Analysis Unit was investigating a human trafficking ring and I was scanning for similarities to my current situation. Who could this Josh be, and why did he need my help? Maybe he was a very busy, headhunting pimp. Maybe he was a shallow blind guy. Maybe he was abusive, or a cheat, or a registered flasher. Maybe he did that thing where he asks subjective questions but acts like there is a right answer.

At the same time that I was indulging my love of worst-case scenarios, I understood that worrying too much about this process was stupid. The LAYYYYDIES were adult women who could make their own choices, and my actual participation was minimal. I didn’t write messages or even gather information that wasn’t public. I should have been able find stunning, smart women and trust them enough to decide if Josh was worth their time.

Sometimes I logged in and thought, “All of these women are so beautiful and smart, this city is so beautiful and smart, hear us all roar,” saving them by the dozen, carefully choosing their best photos and thinking of them as unmet friends. Sometimes I logged in and thought, “Oh, girl, you are not fooling anyone with those angles,” only saving a small selection of ladies, the ones who mirrored Josh’s sample photos. Sometimes I logged in and found it impossible to judge the profiles at all, making excuses for sloppy selfies and misspelled taglines, saving everyone and culling them when I felt more decisive. I wondered if we had dated the same guys, if we went to the same bars, if we had friends in common. It was wearying, much more wearying than it needed to be, as wearying as I made it.

As time went on, I didn’t think so hard. “Nice ladies” and “impressive women” became “this batch” or simply “these.” “See attached!” I obscured. See attached for females. Every email was an implicit, dated “binders full of women” joke. There were no fun stories, just pictures saved and PDFs compiled. Eventually, data entry is just data entry, even when data entry, like Soylent Green, is people.

My payments were slow to arrive. I wanted Josh to use PayPal, but he wanted to send a check. I didn’t want him to know where I lived; I didn’t want to be an open book when he was so mysterious. When his first payment finally arrived, I decided to pull that cloak back. There was no name on the envelope but I plugged the return address and floor number into Google. I browsed through the various enterprises that called this building home. Most were major international companies, unlikely to be owned by my successful entrepreneur, but I found a smaller outfit with three smiling founders. One was a fortysomething man named Josh. His bio said he liked cities and cooking, and valued the happiness of his wife and kids.


I couldn’t be sure that this Josh was my employer. After all the things I’d imagined he could be — pimp, sex offender, human trafficker — married with children should not have been a surprise. But putting a face to the name changed the job, even if it was a case of mistaken identity. When I browsed Match, I pictured the women next to this Josh. I saw them on their first date, their second and their third, exchanging little gifts and sharing expensive dinners. I saw the women’s faces when they learned that he would never be truly available, when they learned that he had children. I worried about these women and this rich married man, these unequal relationships burdened by his wealth and secrets.

My job wasn’t demoralizing to the women; they didn’t know or care that I was preselecting them. The women could have wealth and secrets of their own, with hair big enough to hide it all. They could relish the whole situation, taking to a mistress role with flair. They could turn him down flat. These women could take care of themselves, much as I took care of myself.

There was only one woman who I knew for certain was making herself subject to Josh’s fortune. As unsure as I was about if it was demoralizing to womankind, I was positive it was demoralizing to me. I quit, letting him know that I was sending him the last PDF for free, reveling in the tiny power of not needing his money.

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