How Too Much Online Dating Turned Me Into A Calculated Womanizer

Throughout my years of online dating, I’ve always been asked the same question: “If online dating works so well, why are you still single?”

Here’s the thing: No one ever looks at it from the other side of the spectrum.

Most measure success by whether or not you’ve gotten into a serious relationship or found “the one.”

Of course, success can be measured in many ways; it all depends on how you look at it.

I fully admit to having no clue what I was doing when first starting dating online.

In the beginning, I valued each date as a learning experience.

In the end, I became an egotistical monster.

Success was only measured by how quickly I could feed my ego (i.e. knowing when women wanted to sleep with me).

Before we get to the end, let’s fill in the blanks.

The Male Ego

We all fill our egos in various ways.

The clichéd male fills his with nice cars and lavish toys.

Others lift weights and flex their muscles, proverbially pounding their chests and saying, "Look at me! I’m the man."

While these stereotypes don’t apply to everyone, they do lay a foundation for our self-esteem and perceived social worth.

Heck, half the things men do revolve around impressing women.

Personally, none of this sh*t really did it for me.

Sure, I go to the gym and I’d like to drive a sweet car, but I know most women could care less about that crap.

And the ones that did, I didn’t really care much for anyway.

My ego fulfillment was still based off of women, yes, but I reached deeper intellectual levels to satisfy my needs.

Online Courtship

One of the biggest complaints you’ll hear me talk about concerning online dating is the passive-aggressive approach some women take.

Many get their egos and self-esteem stroked by the amount of male suitors reaching out to them.

Yes, it’s flattering to get all these messages validating that you’re in demand, but is that really enough?

I’d been dating online for so long that only face-to-face validation was good enough for me, and I needed more.

Creating A Monster

A few months ago, I read a book called "Love In The Time Of Algorithms: What Technology Does To Meeting And Mating," by Dan Slater.

He interviewed a guy named Jacob, whom he’d followed throughout his online dating journey.

There was a paragraph about his mixed feelings and perception caught my eye:

Each relationship is it’s own little education. You learn more about what works and what doesn’t, what you really need and what you can go without. That feels like a useful process. I’m not jumping into something with the wrong person, or committing to something too early, as I’ve done in the past.

But he does wonder, "When does it end?"

At what point does learning become an excuse for not doing what it takes to make something last?

He continues,

Maybe I have the confidence now to go after the person I really want, but I’m worried that I’m making it so I can’t fall in love.

It was the first time I had read a story that was parallel to mine, and it struck a nerve.

The difference between Jacob and I was my education.

Besides my personal experience with going on over 100 online dates, I also studied body language and online self-presentation when it comes to romantic relationships.

Add in all the books I’ve read on pickup artists, and I'd gone past the point of no return.

I’d gone from innocent guy who had no idea what to do on dates to a calculated womanizer.

Once I started, I couldn’t stop.

Feeding The Monster

The great thing about online dating is the variety of people you can meet.

There are opportunities to meet both young women still in college or cougars who are fresh off a divorce in their mid- to late 40s.

You can really find anything and everything you want in between.

Given this, I was more focused on learning what worked on women, and I’d say and try stuff just to see if I could get away with it.

Once I figured out what worked for me, I got away with anything I wanted.

It didn’t matter the age or background; if I didn’t sleep with a woman by date three, I'd lose interest and quickly moved on to the next.

I was addicted to first dates.

When most men tighten up and fail, I felt relaxed and thrived.

Through trial and error, I took mental notes on what worked and what didn’t.

When there were avenues to be aggressive, I seized the moment.

I’d stack dates with three separate women Thursday through Saturday.

Each date became a challenge and a game all rolled into one.

At my highest point of debauchery, I went on most of my dates to sleep with them just hours after meeting them.

But sex wasn’t what fed the monster; it was knowing that they wanted to sleep with me.

Sex itself was a mere bonus.

Lessons Learned

Truthfully, there wasn’t much to be proud of.

Sure, there were plenty of notches on my belt, but at the end of the day, there was nothing to show for it.

I became a caricature of myself.

It was as if I played a role in my own drama, creating a persona of Jeremy Grey mixed with Christian Troy.

Why change?

This alter ego I created proved that women gravitate toward confident men who make them laugh with a side of douchebaggery and dash of assh*le.

The old me would’ve been shy, too slow and insecure.

In the dating game, nice guys often finish last.

They’re boring, clichéd and redundant.

In order to stand out from the crowd, I altered my attitude and lured women in by being overly confident, appearing unobtainable.

The harder I played the role, the more successful I was.

I never lied to any of these women or was disingenuous.

They wanted the bad guy; they needed the bad guy.

I just lowered their inhibitions and helped them live in the moment.

Like Jacob, I was worried my online dating success and obsession lowered my ability to find love.

There were plenty of great women I met along the way, but I was too addicted to this online dating game to give any of them a real shot.

Becoming A Monster

When you go on date after date, you become numb to the process.

What’s the point of getting emotionally attached when there’s an unlimited supply of new women on the Internet?

For years, I took this approach, living an extremely emotionally detached romantic life.

The little romance I had was usually faked or half-assed.

Sure, I had a seriously dated few women for months, even years.

But when I became single again, it was like falling off the wagon.

I ran back to what knew to supplement the loneliness.

No need to worry; with a few clicks of the mouse, I'd have new girl in a few days.

When people are skeptical of online dating, they always jump to the conclusion that it doesn’t work, or there are few people to choose from.

No one ever worries about a limitless supply of very desirable options at your fingertips.

We all have our vices, and for years, mine was online dating.

While I’ve put the monster to rest, there’s always going to be a side of me that’s an overconfident, well-calculated romancer.

But these days, I’m more about quality, not quantity.

You won't get love in return when you date to fill an ego.

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