Jul 30, 2023

I Had Sex With Over 300 Women, And Then Got Married

Between the ages of 16-30, I had well over 300 sexual partners.

At a certain point, I stopped counting… but my best guess would be somewhere between 330-380.

When I’ve told select friends this, they are often amazed. How does someone even rack up those kinds of numbers?

In reality, I was absolutely miserable through most of that phase of my life. Because what goes up must come down.

After a number of years, I wondered if I had ruined myself. If I had taken the overindulgence so far that sex had become beyond meaningless. That there would be no magic left in the sexual act to eventually enjoy with my forever partner.

So I am writing this article for two main types of people:

1. Any young men who A) wonder if they should continue to invest energy in expanding the number of sexual partners they’ve had. Or B) are wondering if they can be monogamous after a season of being very un-monogamous… and,

2. Any woman who wonders if it is possible for a man to go from being sexually voracious to happily monogamous. Or, any woman who is curious what the emotional behind-the-scenes is actually like for any player, charmer, or guy going through an as-many-sexual-partners-as-possible phase.

The Early Years

From a young age, I was a very sexual and touch-oriented person.

I started exploring sexually with a friend at 8.

I started consistently masturbating at 11.

I had my first consistent sexual partner at 13.

I officially lost my virginity at 16, and from there, I was off to the races.

The total amount of time that I was single and/or without a sexual partner between the ages of 16-30 was maybe 20 months.

I quickly found that sex was a pleasurable way to enact real-time integration.

If there was some aspect of myself that I wanted to further embody or play with, sex was one of the most effective (and fun) ways to do that.

The default set of conditioning for men was also on my side.

‘Be successful. Make money. Have an abundance of sexual partners.’

So I decided, screw it. Here I go. I’ll sprint up hill and see how many notches I can add to my metaphorical belt.

The Come-Up

From 16-20, as soon as one relationship ended, I would launch myself into another one.

From 20-26 I really doubled down on my sex life.

At my peak I was consistently sleeping with 4 different women per week.

Secretly sad Jordan, circa 2014.

My libido could have done more, but my introversion could only allow me to be around people for so many hours in such a tight time frame.

Being sexual with this many women on a regular basis absolutely fed my ego.

I remember going to a frat party in Southern California and making out with 13 different women within an hour.

I made a game out of it, and I was winning. Not only was I winning… I felt like a god.

I felt like, with this kind of sexual diversification, no one could hurt me. No one could touch me. I had transcended social norms and was sexually free of the matrix.

In my early 20’s I had a polyamorous phase. Because technically, yes, the women I was seeing all knew about each other, as I always made sure to inform them of my relationship status before doing anything with them. But I was absolutely wielding my power irresponsibly. I knew that I had the upper hand in my relationships and I knowingly exploited it. And, I didn’t care. I liked having the upper hand. I liked feeling untouchable.

I would brag to my friends by pondering out loud whether I felt like calling my blonde girlfriend or brunette girlfriend that day.

I once had sex with three women (separately) in the same three-story house party while they were all in it.

I explored a huge variety of sexual experiences.

I went to countless kink parties, fetish parties, and sex parties (commonly referred to as play parties).

I got into heavy BDSM and (consensually) left permanent markings on women.

In this phase, one of my favourite phrases to hear my partners say was, ‘You’ve ruined me for other men.’

And to ensure that anyone I was sleeping with didn’t think that they were the only one I was seeing, I would intentionally leave hair pins laying around my bedroom that matched hair colours that weren’t the colour of their hair.

Now, this will sound strange to some, but I promise you that I have never been more miserable than when I had the highest volume of sexual partners on a weekly basis.

The Come-Down

In Alcoholics Anonymous there is a saying, ‘First, drinking was fun… then it was fun with problems… and then it was just problems.’ This phrase perfectly describes my personal journey with my over-abundance of sexual partners.

At first, my ego loved it.

I mean, if this many women were willing to have sex with me, then it must mean something good about me as a person.

But over time, it became less and less fulfilling.

And then, it just turned into a place for me to hide.

I never had to actually open my heart or get emotionally close to anyone, because there was always another option around the corner.

As the saying goes… the easiest relationship in the world is a relationship with a million people, and the most difficult relationship is a relationship with one.

I vividly remember being in what I rationalized as my polyamorous phase and having a sense of being able to meet my needs through diversification.

If one partner asked too much of me or wanted access to a deeper part of my heart, I already had someone else lined up the following day. Safety net upon safety net. I always had an escape route planned so I never had to risk real emotional availability (or rejection).

When did the initial wave of fun turn into more pain and misery? I would estimate it was in the 20-40 partner range.

For the record, I don’t believe that having multiple sexual partners throughout the course of your life is wrong.

If you’re someone who wants to have sexual experiences with 5-20 people before you settle down into a long-term relationship or marriage, I think that there can absolutely be value in that.

What I am more speaking to is if you’re wondering if it only gets more fun the more people you have sex with, I can assure you from personal experience, it is not.

If anything, it just becomes more isolating. More empty. Less fun.

Rampant casual sex is essentially the practice of disconnecting your heart from your genitals.

Or, as I so poetically put it in a Sex Addicts Anonymous meeting in my mid-20’s, “I feel like I’m draining my soul out of my dick.”

So when you think about it… does that sound like a beneficial long-term strategy?

In my case, it wasn’t. Far from it.

I have very few regrets in my life. I believe that our unique paths lead us to where we need to go and I wouldn’t trade my present-day life for anything. But if there’s anything in my life that I could wave a magic wand and change without it changing my current life, it would be the number of sexual partners that I had. In fact, I would probably take back more than 90% of them.

In retrospect, it is so clear how the vast majority of my sexual partners were engaged with from a place of self-abandonment.

And my body wasn’t quiet about it as it happened.

I would feel sad, hollow, and empty after the majority of my sexual encounters through my 20’s.

During certain phases of this decade, my penis wouldn’t want to ‘work’ and I would override it by preemptively taking Cialis (aka boner pills).

I remember one particular exchange with a woman I had been seeing for a few months. At the end of our sex session (in missionary position), she gently put her hand on the back of my head to guide me towards laying my head on her chest. Immediately, my neck went rigid to prevent such a tender moment from occurring. She looked into my eyes with care, hope, longing… and I looked back with coldness, closure, and distrust. At that moment, all she wanted was for me to take a moment to rest my head on her chest and connect to her with some sliver of my heart. Through my distorted filter, I felt like she was trying to load up on ammunition to use against me at a later date. I figured, the more tense my muscles, the harder I was to stab in the back.

And in my later 20’s, after years of overriding my heart’s dissonance with what I was doing, my body even began tremoring shortly after having sex with certain people. You know… tremoring, like the thing that the body does to shake out trauma? Yeah that.

Despite a bone-deep knowing that I had, for years, been going against my body, I continued on.

It wasn’t until I was about 29 or 30 that I really started to listen to what my heart was saying.

I rapidly cut out frivolous sex. Then cut out sex outside of relationships. Then I decided to take a full year off of any sex or dating.

I wanted a full reset. I wanted to listen to the parts of myself that I had been overriding for years.

A lot of energy moved in that year, and I felt like an entirely new person by the end of it.

It doesn’t register to me as a coincidence that at the end of that year, I met and began dating my now-wife.

I had intentionally cleared out so much old residue through myself that of course this was the time that I had called in my forever partner.

And it also makes sense to me why we hadn’t been a fit earlier than when we met… because I was energetically backed up with so much superfluous, untrue energy.

It wouldn’t have made sense to call in a truly aligned partner when I had been loaded up with so much misaligned static.

Mainlining Married Life

So you might be wondering… how am I doing now?

What is it like for me to be married… fully monogamous… and committed to one sexual partner for life?

In short, I’ve never been happier.

And I’m not just saying that because I need to wrap a pretty bow on this story with a satisfying character arc. I really mean it.

When I look at photos of myself from 10 years ago compared to now, it is wildly apparent.

In photos from 10 years ago, my eyes look sad. I look hollow. I look like a just-getting-by addict with access to an unlimited supply.

Now, my eyes shine. My inner child is so much more present in my face. I look alive.

I experience a deep sense of peace in my life now that the 10-years-ago version of me craved.

As the saying goes, ‘You can’t get enough of that which doesn’t satisfy you.’

10 years ago, I was grasping. Desperate. Searching for a sense of enough-ness through countless bodies. And as a result, I felt miserable, hollow, and alone.

Today, I feel connected, seen, loved, joyful, and at peace.

As for my sex life today…

I have never been more deeply nourished by a relationship in my entire life (I mean, obviously. Why else would I have married her?).

A friend’s father used to say, “Sex with someone new is always the same… and sex with the same person is always different.”

I couldn’t agree more.

The amount of depth, range, and connection available to me in my marriage is unlike anything I have ever experienced.

Even with having had over 300 sexual partners in my varied past, I can see how I was always searching for this. Searching for this sense of home… sense of safety… sense of deep connection.


For the men who might read this and wonder if an endless parade of sexual partners will bring you a deep sense of worth and fulfillment? I can promise you, from personal experience, that it will not.

There is not only a law of diminishing returns, but a law of negative returns, in how unsatisfying this path becomes.

And for any women who are reading this because they’re wondering if a man (maybe a potential partner of yours) can go from having a varied sexual history to settling down and committing to one woman… let me assure you that yes, it is possible. I have tasted (read: binged) the rainbow and know for a definitive fact that I have been 100x more fulfilled in being committed to my partner than I ever was during my season of overindulgence. It is a world of difference. They don’t even begin to compare.

So whoever you are and for whatever reason you’re reading this… I hope that my lived experience serves you in some way. At the very least, I hope that it makes you think.

On a societal level, the narrative of hookup culture, rampant casual sex, and a fear of “catching feelings” is simply a symptom of the people being locked out of their own hearts.

There is absolutely an egoic invulnerability… an emotional hardening… that has taken place. And I myself was a heavy user in said aspect of modern culture.

In retrospect, I would take the vast majority of it back. It didn’t yield positive results for me. And I wouldn’t recommend having an over abundance of sexual partners to anyone, male or female.

And yes, anyone at any stage of their lives can reconnect with their heart… and re-infuse depth and meaning into their sexual intimacy.

Now if you’ll excuse me, I hear my wife starting to wake up in the other room… and I’m going to go make her breakfast.

Dedicated to your success,


Ps. If you enjoyed this article, you’ll also love checking out:

How I Met My Wife

4 Ways To Fully Receive Feminine Nourishment

I Used To Think That Men Who Got Married Were Idiots



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