The Single Most Damaging Thing I Learned As A Pickup Artist

Forget everything you think you know.

man in a crowded room Courtesy of the author

From 2009 to 2012 I worked as a pickup artist. Technically, it was a milder version of the pickup. We taught social skills (conversational agility, eye contact, humor, body language) to people with some level of social anxiety, but it was almost always within the context of approaching and dating women. And sometimes we taught in night clubs. So yeah, basically pickup.

Being in an overlapping version of the pickup industry, I ended up soaking up a lot of the literature of the time. I studied the "greats": Neil Strauss, David Deangelo, and Richard LaRuina. And while this underlying message wasn't expressed directly by all of the practitioners and leaders at the time, one consistent theme across most of the knowledge base was...


Here's what I learned from being a pickup artist: when a man shows his emotions to his female partner (especially sadness), she will hate it, it will turn her off, and she will eventually leave him because of it. 

The phrasing was subtle at first, but it became blunter as the years rolled on.

At first, pickup artists would drop hints along the lines of, "If she sees you being sad about anything in your life, it will flip on her 'mothering instinct' switch and she will see you as a child, and thereby lose all sexual attraction to you."

Then they would get more aggressive with their message and say things like, "If you allow her to physically comfort or embrace you after having sex, she will see you as soft and dependent and will rapidly fall out of love with you. And it won't even be her fault."


In other words, pickup artists of the early 2000s were all peddling a fancily gift-wrapped version of the old, well-known social construct of "boys don't cry." But they were taking it to the next level. They were implying that women were disgusted by emotions and that showing any of them would make your relationship crumble.

If this sounds ridiculous or exaggerated, then you may have not gone as deep into the annals of pick-up literature. Believe me, there is some heinous stuff down that rabbit hole that you probably don't want to ever expose yourself to.

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Here's why shaming male emotionality works, and why they teach it to pickup artists: 

  1. Plays into an existing social construct about male emotionality being fundamentally unattractive.
  2. Simultaneously keeps men's heads and hearts disconnected from one another, therefore making them easier to sell to. As long as men aren't connected to their intuition and emotional body, they are more easily manipulated.

The ramifications of this are that I have worked with dozens of men over the past few years who came to me exclusively with the intention to unlearn what they had learned through their pickup years. More specifically, they wanted to relearn how to engage in healthy vulnerability, and let go of the "keep your cards close to your chest" style of living and relating.

Photo: Author

It's even insulting that the material suggests that women couldn't possibly feel emotionally and sexually connected to someone in the same moment, as if sex and emotions have to be entirely separate from each other (spoiler alert: good sex is all about feeling).


And yet, the stereotype lives on. Just yesterday a guy commented on an article detailing my breakup about how I must have messed up the relationship because I was likely too emotional and that "You should never give her the keys to the castle. You have to keep the eternal mystery."

Yeah, because the key to successful long-term monogamy is to never let your partner see, know, or understand you on an emotional level. Cool story bro.

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So, what is true? First of all, the truth is that this isn't a gendered thing. Have you ever heard of projection? Long story short, people only hate in you what they hate in themselves. So if you have a partner (male or female) who doesn't like that you're emotional, it's because they reject that same emotionality in themselves.


So yes, if you are an emotionally constipated person, then you will more than likely end up with a partner who is emotionally constipated to the exact same degree as you. This is how our attractions work. Whether we're consciously aware of it or not, we tend to attract significant others who match us in levels of self-esteem, self-love, tolerance of intimacy, and emotional congruence and honesty.

For some of the guys who have a lot of damaging pickup literature rattling around in their minds and want to hear it straight from the source, I asked a few of my most eloquent female friends what they thought about this topic:

1. Crying brings us closer together

"When I witness my partner cry and am able to hold space for his deepest fears, I feel the deepest sense of honor. It is an honor and a privilege to be there with him in his more emotional moments. I know how much of a brave face he has to put on in his daily work life, so to be able to support him through his tears is an honor that I wouldn't trade anything for.

And yes, to answer your second question, I not only am still attracted to him, but we often have some of our best sex immediately after he cries in front of me. I feel that much more connected to him as a man when he cries... I don't feel distanced or turned off at all. If anything, it's the opposite." Chelsea, 32

2. It's easy to tell when he's holding back

"If my boyfriend holds back his feelings or fears from me, I can feel it. I can feel it when the pressure is building inside of him. So it feels like a gift by the time it comes out. Not because it was a burden before, but just because I know that he and I will both feel better and more deeply connected after we've been able to help him move through whatever he's holding on to." Polina, 27


3. Vulnerable men make the best partners

"The truth is that no matter what initially attracts us, it's a man's vulnerability that we stay for. Not because we want to mother our partner, but because we want someone to also be vulnerable with." Diana, 44

4. One can appreciate showing vulnerability

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"While I don't have a kink or fetish for tears per se, I definitely appreciate it when my husband cries in front of me. I know that humans are emotional beings, and if I never saw him cry then it would feel like he was lying to me on some level. Like he was knowingly holding his truth back from me. And that [him not ever crying in front of me or allowing me to support him] would definitely erode the relationship way faster." Jean, 42

What evidence is there that men's emotions aren't unattractive?


I could take the solipsistic route and give examples of "I'm a highly emotionally attuned guy and I've never had a problem finding a relationship partner," or the slightly more removed, "I know that my father/grandfathers cried with their wives and they cumulatively have over 130 years of marriage between them, and their relationships were all better for those tears shed," but that might not be relatable enough if you don't know me personally.

Think about it: Do you hear of more relationships ending because of too much emotional intimacy, or because of too little emotional intimacy?


Photo: Author

In relationship researcher John Gottman's studies, time and time again emotional intimacy was one of the key factors in maintaining a thriving, long-term relationship. On the other side of the spectrum (that did the most damage in relationships)? Stonewalling and defensiveness.

Simply put, the more that couples leaned into each other (as opposed to retreating or leaning away), the better the relationship did.

So if you learned that women would run for the hills as soon as you started tearing up, good news: that is only true if your partner is afraid of emotions themselves. If you are a man reading this, you are not doomed to a life of stuffing down your emotions (unless you meet and attract a partner who expects this of you, which in itself is a lesson for you to explore and unpack).


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Jordan Gray is a five-time #1 Amazon best-selling author, public speaker, and relationship coach with more than a decade of practice behind him. His work has been featured in The New York Times, BBC, Forbes, The Huffington Post, and more.