Confessions of a digital pick-up artist

I’m standing on the field of a large sports stadium. The stands are packed with women. They aren’t angry, just disappointed. One by one they look me in the eye and ask one simple question: ​“Why?” I wake up and decide it’s time to quit ghostwriting dating emails.

My life as a bargain-bin Cyrano de Bergerac began in 2009 with a Craigslist ad. ​“Creative writers wanted,” it said. I was living in Buenos Aires, barely scraping a living and at least six years too old to be on a gap year. I applied.

I was sent a few bullet points about a hypothetical guy (likes the smell of fresh cut grass and long walks on the beach, that kind of thing) and four links to the dating profiles of real women on Match​.com. As a test I had two hours to write an email from him to each of them. Looking back on what I wrote now, I have no idea how I got the gig. ​“There’s nothing quite like a day spent on the high seas is there?” I asked one unfortunate woman. I lavished another with the oddly passive aggressive compliment: ​“looks like you know how to appreciate the great outdoors”. And then there was this line, which is making me retch as I copy and paste it: ​“I am a three-time Hungry Hippos state champion, so I like to play hard myself.”

This drivel somehow got me summoned to headquarters, a sparse but swanky flat in a well-off neighbourhood in northern Buenos Aires. It belonged to the founder, let’s call him Steve*. Steve was an American guy in his mid-20s who was living out his entrepreneurial dreams against the backdrop of a favourable dollar-to-peso exchange rate. He came ​“from a sales background”, a fact he would use as an excuse for being an arsehole on multiple occasions. He also had a tic which involved placing his outstretched hand flat against his face then slowly dragging it downwards, squishing his nose and dragging his cheeks down to expose his lower eyeballs. I think it was a sign he wasn’t happy.

Steve let me in on the inner workings of the machine and my place within it. The clients, at that time all straight guys, paid a monthly subscription. In return the company would write a dating profile for them, supply them with lists of potential matches and handle the correspondence with those women for as long as the client wanted. That could be anything from making the first move on a dating site, to coaching them up to the moment they walked down the aisle. I was a lowly ​“opener”, the guy who sends the first email to an unsuspecting victim in order to break the digital ice. I got paid a flat hourly fee which came to about £4, then a bonus for each response I got which wasn’t negative. And boy could it get negative. One of my beautifully crafted missives was met with the response: ​“get lost, you ginger stepchild”. As an opener, I learned to get used to such hostility.

I was writing for four or five guys at any one time. I never had any direct contact with them, but I did get a little fact file on each, covering their personality and what their preferences were when it came to women. I knew that Larry* was pitching a TV show, liked AC/​DC and was into all kinds of girls except African American ones. Mark* loved sailing but hated closed-mindedness. Richard* had met Britney Spears and would ​“put up with sushi for women”. Then there was Howard*, who made a lot of money as a doctor and wanted everyone to know about it.

After I’d read up on my guys, I had to trawl various dating sites looking for women I thought they’d like. This was weird. We’re talking 2009 here, when the online dating world was a more innocent place. No Tinder, just people putting themselves out there in a very genuine way, with quite long and often vulnerable bios on sites like Match​.com and eharmony. These women had no idea their words and looks were being assessed not only by a potential suitor, but also by a poorly paid hack in his bedroom. I would regularly get in trouble with boss Steve for not judging women harshly enough. Here’s one piece of heartwarming feedback: ​“not sure if she’s hot enough for this… the rule should be like 7s and above… this girl is probably a 5.”

Once I had a list of profiles the guy was interested in, it was time to write the opening email. During the test I had naively assumed the key to this was a sense of humour and aiming for some kind of empathy. I was wrong. Steve told me the secret was to use techniques based on the world of pick-up artists, the kind of stuff you’d find in Neil Strauss’s best-selling book, The Game. If you want a little taste of Strauss’ methods go to YouTube and check out the Jimmy Kimmel interview where he tests his wares on Jessica Alba. It’s a painful watch and not only because he’s wearing an ill-advised t‑shirt-over-shirt combo.

I couldn’t bring myself to read The Game, but Steve drip-fed me entries from its lexicon of douchebaggery. There was ​“peacocking,” which meant wearing a consciously ludicrous item of clothing just to start a conversation. Peacocking is largely to blame for the sharp increase in fedora sales in the mid-2000s. ​“Negging,” was a key weapon for any opener. As far as I could understand, it involved making a slightly negative, even bitchy comment, usually to someone who was more attractive than you. For my sins, here’s one I actually sent: ​“I was looking through all these profiles here on OKCupid thinking to myself, ​‘Look at all the poor, desperate, lonely women…’ and then I saw your profile and thought to myself, ​‘Hey, here’s a poor, desperate, lonely woman that’s actually CUTE.’” Negging is also known as being a dick. I’m not proud of it.

“The power” was something I had to be prepared to fight for at all costs. To get the power I had to ​“challenge,” women almost constantly. This meant provoking them into proving themselves to you in some way. The shortcut to this was to add, ​“if you think you can handle it,” to the end of any sentence. Here’s another one I wrote earlier: ​“Let’s get together for a cup of something delicious and some interesting conversation… if you think you can handle it, that is!” I’m not quite sure how she wouldn’t be able to handle the combination of drinking and chatting, but I’m happy to admit this was not my finest period artistically.

As a special treat, Steve once sat my fellow opener, Michael, and I down to watch these nefarious techniques being put into action. He’d been selected to feature in the pilot of an MTV show about dating and the first edit had just arrived. As I remember it, he was one of three contestants who had to find a girl on a night out and leave with her, or at least her number, in an hour. His white fedora was easy to spot, even in the dim light of the club. He was peacocking with the best of them, firing off negs in all directions like an unattended fire hose. When they didn’t land he squished his hand against his face and moved on to the next victim (pick-up artistry is a numbers game). I can’t remember if he won. In truth it was hard to think of anyone involved in the show as a winner. When the episode finished he turned to us expectantly. We were speechless. Was this really how you had to act to cop off?

As time went on I developed favourites within my stable. Richard was a widower who just seemed low on confidence. He was in his late 40s with two kids and I felt protective towards him. When he got negative messages I tried to go in and delete them before he saw them. Richard was the guy on the wrong end of the ​“ginger stepchild” comment and I felt guilty for days afterwards, knowing he’d read it. Others I was less fond of, like Howard, who had a very different vibe to Richard. He soon tired of conventional dating sites and dragged me on a journey through the more carnal delights of Elena’s Models and SugarDaddy​.com. He wanted to get laid, basically. Nothing wrong with that, but paying someone to make it happen on your behalf seemed like a strange way to go about it. Writing for Howard made me feel even more conflicted about a job that was already making me uncomfortable.

In my year of digital deceit I only ever heard of one silver lining. A guy called up Steve for dating advice after he’d been on over 20 dates with the same girl. A week later he cancelled his subscription. I was really happy to hear this, but I couldn’t help wondering whether he would ever come clean about how they’d met. How do you even do that? And when? ​“Funny story, just a little thing really, but the first message you got from me on Match​.com was actually written by a 27-year-old guy from the Home Counties in the midst of a quarter-life crisis. Mad, eh?”

Recently I’ve been wondering whether this man was the only one who made a success of it. How did the rest of my boys feel about the experience ten years later? With limited internet sleuthing skills I tried and failed to find out. I discovered Richard’s political allegiance (Republican), the town where he lived (somewhere in Florida) and how much he’d paid for his house (a lot). I tracked him down on Facebook and even on LinkedIn, but my messages went unanswered. I guess a business networking site may not be the ideal place to start a conversation with a guy you’ve never met who tried to hook you up with women a decade ago.

Undeterred by this abject failure, I went straight to the source, Match​.com. Maybe I could track them down with a fake profile, try and catfish the catfishermen. I used the overlapping preferences of a few of my guys to build my persona. I’m 5ft 5in, my body is athletic/​toned, I don’t smoke, I don’t want kids and I’m a social drinker. I’m white (inevitably), spiritual but not religious and 36 years old (I assumed my guys’ desired age range was growing with their own, rather than taking the 25-and-under DiCaprio approach). To find a photo I did a Google image search for ​“American woman 36 years old”. Turns out people only get described in this way when something terrible has happened to them. The images I clicked on were attached to headlines like: ​“36-year-old Texas woman is on life support after going to Mexico for plastic surgery,” and ​“Canadian woman who went missing in Belize and her boyfriend found dead, investigation continues”. In the end I settled on a photo of a Utah woman who was renting half of her ​“duplex uterus”. Then disaster struck, just as I was getting excited about picking my own username and writing a profile, Match​.com told me there was a problem with my new account and I could go no further. It was as if they knew what I was up to. The catfish had been caught.

There was a lot I wanted to ask my guys. I wanted to know if they saw this kind of service as a temporary solution or a genuine approach to meeting people. On the face of it outsourcing your dating to someone else seems lazy, or even fraudulent, but I don’t think that’s necessarily the case. With attention spans getting shorter and the internet already full of pictures of people who are better looking than you, making yourself stand out as an attractive and unique individual was a hard thing to do on a website in 2009. Arguably, it’s even tougher on an app in 2019, so is there really anything wrong with hiring someone who’s good at that stuff to do it for you, as long as they’re not misrepresenting you? Part of me thinks, what’s the harm?

But then I think back to the grubby tactics of the pick-up artist, which formed such a large part of what we were doing. Does their manipulative approach to seduction have any place at a time when two-thirds of UK universities are bringing in sexual consent training for students? Strauss himself seemed repentant when he spoke to The Guardian in 2015 about the legacy of The Game: ​“It was really a book about scared men who were afraid of women. But then it became a part of the culture. And it became a reason for women to be afraid of guys,” he said.

In the era of #MeToo people are questioning why a pick-up artist’s manual is even available to buy. Earlier this year Sarah Green, co-director of the End Violence Against Women coalition, asked publisher Canongate to stop selling The Game and its sequel, Rules of the Game, saying: ​“This view that women are there for you, and that you can treat women in bars like they’re not the same kind of human as you, is over.” That’s exactly what we did; we treated women like another species. They were strange prey and our job was to snare them after studying their habits.

There was also the feeling that the whole enterprise was transactional — I was the means people used to get their end away as quickly as possible. The goal was to shorten the gap between first contact and consummation and that’s been the way love in the age of the internet has been evolving ever since. As my professional interest in online dating was ending in 2009 Grindr was just getting started. Its groundbreaking use of location data made impromptu neighbourhood hookups possible without leaving the house. Tinder followed in 2012 and ​“swipe left” and ​“swipe right” entered the vernacular. Now that we could accept or reject in a fraction of a second, it seemed we’d won the race, we were dating with ultimate efficiency.

But efficiency just isn’t that romantic. Dayna Evans pronounced Tinder dead in Gawker in 2015, writing: ​“by allowing us to play into our desire for a simple, no-frills path to hookups and dating, the swipe-right culture makes you start to feel like everyone looks and is the same. Tinder gives us what we think we want, but without the spark or intrigue, or any of the human effort that normally goes into sex and dating.” That human effort was reduced even further by apps like Bernie which used AI to work out who you were into and then did the swiping for you. Although the developers’ stated goal was to make more matches happen it’s hard not to see it as another step away from human connection.

Things are starting to shift. The Guardian reports that personal ads, long seen as the refuge of local paper bothering misfits, are making a comeback on Instagram and Twitter. Personal ads make it feel like someone’s put the brakes on our frenetic modern dating experience. It takes time to write your own ad and, more importantly, it takes time to read someone else’s. You can’t just discount them at a glance. With people feeling burnout around dating apps in general, could this be the answer? The pressure of immediacy is off. You don’t feel like you need to be constantly on the lookout for matches and if you want to reply you can take your sweet time instead of worrying about exactly what subliminal message your response time is sending.

For my part, my experiences as an on-loan lothario have made me warm to the luddite approach. I’m in favour of anything that encourages authenticity, that gives you more space to be yourself. Basically the opposite of the messages I manufactured for guys and sent to unsuspecting women. I’d still love to know what those women think about it all. Maybe a few of the guys came clean and it was all totally fine? Hearing that would make me feel better about my role in the whole business, because I’ve never felt great about it. I still lasted a whole year, I think because I was waiting to be judged, for someone to pull me aside and say, ​“Rory, what the hell are you doing?” The problem was people were too fascinated by the whole bizarre operation to question whether it was really an appropriate way for me, or anyone, to earn a living.

In the end it took a creepy dream where a stadium full of women looked like they might kill me to bring me to my senses. After over a thousand passive aggressive emails sent on behalf of men I’d never met to women who didn’t even know I existed, I gave up being an opener.

*Names have been changed.