Interviewing the pickup artist who hit on me

My journey into the murky world of day gaming

I was walking along Bondi Beach the other week when a man, in his late 20s or early 30s, stepped in front of me. He did an exaggerated wave, like someone cleaning a car window, as he cut in front of my path. 

“Hey, I just wanted to say that I really like your style,” he said gesturing in the direction of my body. 

I had just been to the gym and was wearing a stained shirt I’d jaggedly cut into a crop top using blunt scissors, along with an old, faded puffer jacket. There are so many things a person could justifiably accuse me of being. Stylish is not one of them. 

But this is not the first time I’d been stopped by a sweaty-looking man offering me an ill-fitting compliment.

“Are you day gaming?” I asked. 

He looked shocked – they always do.

“Uh…” 

“Are you?” 

“....yes” he mumbled. 

I nodded. 

“Good luck out there,” I said walking off. He stood there for a moment, before scurrying away the opposite direction.  

This interaction, in various forms, has been happening to me since I was in my mid-20s. 

I’ll be walking by myself, usually in Sydney’s CBD, and out of nowhere a man will appear directly in my path. He’ll say that I look so interesting, so beautiful, so kind, so whatever he thinks will flatter the most. If I continue to engage, he’ll ask for my number. Sometimes, more rarely, he’ll immediately offer to take me for a coffee or a drink. 

In isolation, these were strange one-off interactions. Moments you’d chuckle about that afternoon with friends, but forget a few weeks later. It took years until I realised these conversations all followed a pattern. These weren't happenstance meetings. I was being targeted by different men all using the same formulaic method. 

That’s when I did some research and learnt that I was being approached by day gamers.

Day gaming is a subgenre of the murky world of pick-up artists. These are, as the name suggests, men who try to master the art of convincing women to have sex with them. But rather than using boring and time-consuming techniques like finding rapport, building mutual chemistry, and allowing feelings to grow, they prefer shortcuts. Sometimes this means preying on a woman’s insecurities or using tactical insults known as ‘negging’. Other times — and in the case of day gaming — it means pretending love and fate have collided with random women on the street.

These men will set themselves up in busy areas and approach dozens of women with the same, tired compliments. If the chosen quarry engages, and the conversation goes well, they’ll try to get her phone number. The eventual goal for some men is, of course, sex. Others think of it as a viable alternative to dating apps.

There could be dozens of day gamers in this photo for all we know.

It was on a late afternoon walk, a couple of years ago, that I met a day gamer called Jonathan (I’m using a pseudonym). I had been heading towards the supermarket, just as the sun was setting, when I was stopped by a man wearing chinos and a collared shirt. 

“Hey, sorry to interrupt you,” he said. “I just wanted to say that I think you’re adorable.”

Jonathan would later tell me that I was the second woman he’d stopped with exactly the same line.

“Jonathan!” I said as though I were greeting an old friend. “Are you day gaming?”

Day gamers are always shocked by this question. Often their mouths will open and close a couple of times, like an actor with stagefright. Some will attempt to regain control of the conversation. Others become defensive, “what if I am?” one man once replied. Most, however, drop the character and are willing to have a frank conversation. 

Jonathan sheepishly admitted that, yes, he was day gaming and we had a brief chat. At the time I was considering doing an audio documentary on pickup artists. I asked if he’d be interested in recording an anonymous interview with me after work one day. We both had offices in Macquarie Park at the time, so he agreed. 

A couple of weeks later we sat together in my company’s small, dark studio. Jonathan fidgeted in his seat as I set up the equipment and did some sound checks. I asked few gentle questions to ease him into the interview – I quickly realised Jonathan had a stutter which became more pronounced when he was flustered. He was clearly nervous, why had he agreed to the interview? I pressed the record button.

Jonathan told me he found day gaming after reading Neil Strauss’s book The Game – a seminal text for pickup artists and a gateway for many people in the scene. Fascinated by what he’d read, Jonathan wanted to learn more. Luckily there was a wealth of material out there — particularly on YouTube — which expanded and evolved the techniques outlined by Strauss.

Beware of men who have this on their bookshelf

“I found it improved my confidence,” Jonathan said. “I'm naturally an introvert, very shy. I had my first girlfriend when I was 23 years old. I use this as a way to build my self confidence.”

Approaching strangers with romantic intent, dead sober and in the harsh light of day, would be hard for anyone. Jonathan seemed more socially ill-at-ease than most.  

 “Why would you put yourself through that?” I asked.

“People who are overweight force themselves to go through the discomfort of going to the gym,” he replied. “It hurts, it's painful, but they see the the better outcome on the other side. So it's a similar thing. I'll put myself through rejection hoping that it will make my skin thicker.” 

By now Jonathan should be one, big callous. Rejection is a constant in his life. A typical day gaming session for Jonathan lasts around three hours, during which time he’ll approach at least 15 women. When Jonathan’s motivated, he’ll do this every Saturday and Sunday. Most women will only talk for a few seconds before finding an excuse to scurry away. 

But if you approach enough people? Eventually you’ll have some luck. 

“I'm happy to say that most of my long term relationships were from a day game,” Jonathan said. 

“Do they know that you were day gaming them?” I asked.  

“No, I don't think that they knew. They might have thought that I was chatty, but I don't think that they knew that I was doing this every single day.”

“How do you think they would have reacted?”

“Good question,” he said. “I-I think it depends on how open minded that they are, so if they're more accepting, they'll probably accept it.”. 

Questions which called for self-reflection made Jonathan’s fidget in his seat, like a child waiting for recess. I pushed a bit more. 

“Think of one girlfriend you got through day gaming What would she have said if you had told her?”

“Yeah, I-I cannot guess on-on what they’d think. Probably there's a more chance that they think negative-negatively of it.”

“Day gaming is devoid of romance or chance or fate,” I said. “You're dating in a really mathematical way.'“ 

I don't think of it as mathematical,” Jonathan said after a pause. “You are right. The more I approach, the higher the chances of having success. But if I could have had just one wish that if I just approached one girl, and we got married and lived happy life ever after. Then I would wish for that.” 

At the time of the interview, Jonathan was 37 years old. He’d been day gaming on and off for a decade. When would he stop? 

“When I find the partner that I can settle down with,” he replied. 

I can’t agree with what Jonathan or his day-gaming ilk are doing – it’s cynical and manipulative. But so help me, I’m empathetic to them as well. Dating is hard. It’s a long slog through rejection and bitter disappointment.

These lonely men – probably afflicted with more of those negative experiences than most – have gone in search of another way. Pickup artists have told them that seeing women as just numbers and approaches will make things easier. Less personal. As though the pain of rejection is something a person can be inoculated against.

But love and suffering are so intertwined they may as well be conjoined twins.

To love a person — even in the earliest of stages — you must first accept that they could hurt you. You can’t escape that exquisite vulnerability. But who would want to? All good gambles come with risks. You just have to be brave enough to roll the dice.