Over And Over Again

Over And Over Again

I often talk about my time immersed in online dating. I speak about it in the way that people reminisce about their college days or how people speak about their childhood. A moment in time where we were so absorbed in a culture that it was difficult to imagine a life outside of those moments. I don’t use the word “culture” lightly. Maybe it isn’t so easy to see if you casually date online, but when you dive into the deep and obsessive places that I found myself for years, well, you learn the words, phrases, beliefs, and way of thinking that is unique to those of us who allowed online dating to dominate our every day lives.

If you do anything over and over again for long enough, you will begin to see patterns. Little nuances that when examined closely enough, unintentionally cause you to become a person fixated on maximizing their potential. And it all sounds so cold and calculated, but really, it is simple refinement. And truthfully, for the better.

“Wait, Chris – so you’re saying that it’s a positive thing to flirt with people over and over online?”
What I mean is that by doing anything over and over again, you learn. It is inevitable when you interact with other humans tens of thousands of times to not pick up to what they find appealing. And yes, as I type this I am fully-aware that it comes off like some social experiment but the truth is that just because I paid attention doesn’t discredit the validity or sincerity of my words. I met some amazing people that are wonderful friends and I dated a handful of women very seriously through this process. But I only got that opportunity because I learned how to become a better version of myself through the trial and error.

As a man, I was raised by a wild pack of terminally horny friends who seriously lacked in the communication department. As with most guys, we bounced ideas and stories at each other and we paid attention to our peers, because if what Mike did with that chick, well, it must work with all chicks, right? And unfortunately, this is the prevailing immature attitude with so many people in the world. And we are a product of our environment. If we surround ourselves with people who don’t have the ability to convey honest emotions, we will be influenced by that behavior. So when you contact people over and over again saying words and phrases with the underlying attitude you learned from a bunch of dudes who fart on each other and are scared to expose their true feelings about anything, you will begin to notice a pattern. And that was a pattern of women being either disgusted, upset, or simply turned-off. And it wasn’t like I was trying to be a jerk – I simply didn’t know any better. Oh, sure. I knew how to give a compliment, but I didn’t know what interaction was about – it was about establishing a connection through mutual respect.


A word that I can guarantee was never spoken in our late-night farting sessions. The idea of speaking and then listening. Not just waiting to talk, but to hear the ideas of another person. And I learned so many lessons. I learned how the most important thing you can do for another person is to make them feel loved and appreciated. And then I learned HOW and WHY to make them feel loved and appreciated. And what I also never learned is that the more you nurture a relationship, the more you fulfilled and content that relationship will make you.

I learned the secret to a healthy relationship is that what you give should be relatively proportionate to what you receive. And the way I learned this was by women giving me a slight slap on the wrist when I said offensive or insensitive things to them on a message on a dating site.

It is not your responsibility to raise anyone but your children. And you certainly are not obligated to correct anyone’s behavior. But I will tell you this – I am a better version of myself because thousands of women gave me feedback. Some with a brutal smack and some with an affectionate yet disapproving head shake. But I paid attention and I learned through trial and error and began the slow process of removing the negative behaviors instilled by scared and repressed little boys who grew up into scared and repressed men. But mostly, I learned how to listen and take criticism.
So I could be better for you.

About author

Christopher Gutierrez

Christopher Gutierrez is the author of several books on love, sex, and relationships. He also hosts a weekly podcast, The Deep End, in addition to running Deadxstop Publishing. Since 2006, he has given hundreds of speakings at colleges, coffee houses and universities all over the world.

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