How a Top Pickup Artist Went From Orgies and Bondage to Becoming a Family Man

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In 2005, Rolling Stone writer Neil Strauss released his book “The Game,” which chronicled his years-long journey in the seduction community. These communities provide men who moonlight as pickup artists the opportunity to get together to share and learn ways to court women. Strauss’s book follows his interactions with the women he was trying to woo along with his pickup mentor, known as “Mystery.”

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The book was a hit and brought the once underground pickup artist community into the mainstream. It also created an explosion of businesses aimed at helping men improve their skills in socializing with women. Some of these businesses offer weekend “boot camps” for men to train with pickup coaches and get real-life experience talking to women and can cost thousands of dollars.

Since its release, “The Game” has sold 2.5 million copies and has made Strauss a celebrity amongst men looking for pickup strategies to improve their dating lives.

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“It’s super weird,” Strauss tells NextShark. “My phone started ringing and guys were asking me for advice on women. I just thought they would go to the book for advice. I did not think I would be a representative of the lifestyle.”

Around 2010, Strauss entered a long-term relationship with Mexican-born model Ingrid De La O. While Neil says their relationship was the best he’d ever had, he couldn’t stop chasing other women. At one point, he was caught cheating on her with one of her best friends inside a car in a church parking lot.

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Although De La O was hurt, she agreed to forgive him if he checked into rehab for sex  addiction. During his three months in the mental hospital, he was diagnosed with generalized anxiety disorder, depression, sex addiction and ADHD.

Strauss and De La O got back together after he left rehab but broke up again shortly after. From there, Strauss went on a slew of sexual escapades. He had a fling with a string of women including a Vegas showgirl and a Silicon Valley entrepreneur and experimented with BDSM. He documents in his book his experience attending a swingers club in Paris, France. The club had naked women lying on mega-beds with men wearing suits with their pants unzipped, exposing their genitalia.

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Strauss detailed in his book: “The scene on the beds is basically what Muslim martyrs are promised in the afterlife, except with virgins. But paradise is here. Now.”

At one point, Strauss even lived with three girlfriends under one roof in Los Angeles, writing, “It turned out to be the worst orgy of my life.” However, Strauss says these experiences didn’t give him the fulfillment he sought, and he ended up checking into rehab again to cure his sex addiction once and for all.

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Fast forward to present day, Strauss has invited NextShark to his secluded home in Malibu near the beach where he loves to surf. He’s now 45 and married to De La O, 26, after reconciling with her in 2013. Their marriage was also timed with the symbolic funeral of his pickup artist alter ego, “Style.” Last spring, Strauss became a father with the birth of his son, Tenn.

“One thing you should know: I do everything on Mondays,” Strauss says. “All my meetings and appointments are stacked back to back. That’s why today is hectic, but I make it hectic on purpose so I have Tuesday to Sunday to write. I feel like it is one of the things that makes life go well.”

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Today, Strauss has completely distanced himself from the lifestyle featured in “The Game” and focuses instead on a monogamous and meaningful relationship with his wife. He documents his journey to this point in his new book, “The Truth: An Uncomfortable Book About Relationships,” which he initially wanted to call “Game Over.” Neil started writing the book six years ago with the intention of explaining how monogamy was outdated only for it to morph into something that he considers much more meaningful.

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“‘The Truth’ is a much more authentic journey to me than ‘The Game,’” Strauss says. “If I look at that book now, the first 100 pages of my thoughts and ideas have changed so much that I do not even agree with them anymore (laughs). And by the end of the book it refutes them. If there was a nice comparison between the books, a lot of the ‘The Game’ is about changing behaviors, and ‘The Truth’ is about changing beliefs. It’s harder to change a belief, but the shift is permanent.”

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Strauss says that if “The Game” is a bible for dating, then “The Truth” a bible for relationships.

“When you are dealing with relationships, all kinds of deep psychological factors come into play that are outside of our awareness. Ultimately, what I found out is the key to relationships is the relationship with yourself. It’s your deep inner game.”

When asked when the last time he tried hitting on a girl was, Strauss says he can’t remember.

“Even if I was single, I do not think I have the need anymore. [‘The Game’] served it’s purpose like training wheels. I’m grateful for the place it got me to. It’s like college: there is no way I would go back to college and study for all those tests, but I’m grateful that I went to college. It taught me a lot of things that I could change. If you follow ‘The Game’ your whole life … it’s pathetic. They need to read ‘The Truth,’ which gets to the deeper stuff of what I was aiming for.”

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Strauss notes in his book that one of the biggest defining moments was after he got caught cheating on his wife and then entering rehab. When asked whether he would have had this current revelation if he never got caught, Strauss says:

“No — good point. I think getting caught was the best thing that ever happened to me. I thought I was an honest and ethical person, but then finding out that I was lying to the person that loved me, just for sex that wasn’t that good anyway, it made me see why I would understand doing something like that. Anytime you see these big incongruencies, there’s evidence of [something] underneath. When I’m coaching guys and I hear there’s distortions in their thinking or things that really contradict, I usually get deeper and find a wound underneath.”

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According to Strauss, those things that are underneath start with our childhood. In an interview with the Atlantic in October, Strauss said that he; Robert Greene, who wrote “The Art of Seduction”; and Tucker Max, who was known for explicitly documenting his sexual escapades with women on his blog in the early 2000s; all share one commonality:

“We all have narcissistic mothers. So what happened? What happens when you grow up with your identity being squashed by this mother who never sees you but only sees herself? You grow up with a fear of being overpowered by the feminine again.”

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When asked what some of the biggest things he’s learned about relationships are, he talks about the importance of transparency and honesty in a relationship.

He tells NextShark: “In the end, the book is the most positive thing that ever happened in our relationship because we literally have no secrets. There’s nothing in my life she doesn’t know and I think that’s a safe place to be for both of us. Some people are really offended with the idea of being honest with your partner, which is insane to me. If there’s one place we have to know the truth, it’s in an intimate relationship. A lot of people have these unrealistic expectations that their partner has to approve and support everything, which puts them in an insane position.”

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In an era where online dating apps like Tinder are the norm, Strauss personally believes that nothing about the social dynamics of picking up women has really changed.

“I think human nature is always essentially the same. Some of the tools we have are maybe different. To me, social intelligence is the same whether you’re in-person or online. Ultimately, the same skill set applies.”

“Aziz Ansari was talking to me about the book he just wrote and we would go through people’s text messages and I could see the places where they blew it. It’s the same places they would blow it in real life. The would not pick up on a hint to get together, or they’d get too needy and push too hard for a meeting. They would make all the same mistakes.”

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“The one thing nice that’s happenings now, you can actually see the text messages and identify exactly where something went wrong, which is interesting. I was talking with one of the guys that started Tinder. He said one of the reasons he started Tinder was ‘The Game.’  He said that he didn’t to want to do all this extra work and wanted to know immediately whether someone likes him or not. So that’s one of the things that’s nice about Tinder — you have the advantage to know when somebody already likes you. But, you can still blow it from there.”

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Strauss says a lot of the things he did in “The Game” came from his poor self-esteem. Because of the trauma he suffered growing up, Strauss aims to not let history repeat itself with his son. When asked what advice he’d give to his son if asked how to woo women, he said:

“I’d probably give him the best advice that is appropriate for his age. My ultimate hope is that he has enough inner confidence and self-esteem that he doesn’t have to worry about it. I hope I’d raise him in such a way that he could enjoy reading ‘The Game’ as a story and not for the techniques.”

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Shortly before Tenn was born, Strauss wrote a letter to him, sealed it and sent it to the address they are living at now.

“I wrote him a letter before he was born just saying, hey, your mom and I love each other and we wanted to have you and you were born out of love — so no matter what happened in his life he knows that he comes from a solid groundwork of being loved and wanted.”

“The letter is postmarked to prove it was written before he was born. It’s proof. You really know where your parents were at, where their heads were at when you were born. It’s a document you can’t deny.”

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Neil is already finishing up his next book, a biography of a legendary musician he has yet to reveal. Check out his new book The Truth: An Uncomfortable Book About Relationships.

Photography by Melly Lee

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