One Thousand First Dates

One Thousand First Dates

After telling someone you’ve been on over one thousand first dates, you can expect to be asked some questions. Some common questions are: “So tell me about the worst one.” “Tell me about the best one.” “Tell me about a crazy one.” And once they feel comfortable enough, the inevitably whispered, “So how many of them did you bang?”

Sometimes I entertain the questions, but most of the time I deflect and move the conversation on to a less salacious topic. I save all the entertaining stories for late nights with friends over pizza… and a book or two, I suppose. But the most common question I am asked is, “So what do you feel you learned the most.”

It’s really difficult to pinpoint the exact aspect of human nature that I gained the most insight, but I can tell you that it is without a doubt, the most dense and comprehensive information I have ever taken in on any subject ever. Now I know that sounds cold, as if each date was some kind of social experiment and not a walking talking individual, but if you do anything enough times you will gain knowledge on whatever it is that you’re involved with whether you like it or not. And while I never went into meeting anyone with the false representation that I would write about our interaction (even if they asked me to), I did take mental notes. As a curious person by nature, I enjoy learning what motivates and inspires people. I am fascinated with the idyosyncracies of people and their approach to attraction. To put it in perspective, I would often stare at the person as we were just into our second minute of our first date – anxiety and nerves at their peak, and just watch their facial ticks. I would watch as they tried to get comfortable in their chair and how they continuously pulled their pants up over their stomach. I listened to the words they fumbled over and what they thought was good first date story material. It’s very telling what a person will lead with. I like to leave the conversation open ended just to see where they take the conversation. Nervousness is an interesting ingredient, especially with someone who is unaccustomed to meeting a stranger in public for coffee. It’s that nervousness that causes word-vomit and makes some people blurt out whatever is on their mind. And it’s so adorable to watch a person squirm while they attempt to back pedal and recover from talking about their ex-boyfriend while my coffee is still warm. But I never held it against them.

But I guess the real answer to that question is, I learned more about myself than anything. How I respond to a person’s callous nature. How I handle second-hand embarrassment when a date accidentally tells me she loves me 15 minutes after meeting (true story). How I handle a racist. Entitlement. Arrogance. But not only how I respond to these things, but how to manage the feelings they stir inside me.

I learned that there is more than one way to approach dating, and life in general. And that no one way is perfect or will work with everyone. I learned the importance of doing my best to leave someone better off for taking the time to meet me. Whether it was to make my corner of the world a little less shitty, or to attempt to make them think, or simply leave them with a smile – I was constantly cultivating new ways to inspire my dates. Maybe as a thank you, maybe because I actually believe the words I write, or maybe because of my deep-seated self-loathing that constantly makes me feel like everyone should leave with a parting gift just for taking the time to walk through the door of my low-rent haunted house of a life – but really, that’s probably just the 2am talking right now.

Whether we just left with an “I’ll never see you again” hug, a two hour chat and a hook up, or the beginnings of a relationship, I did my best to pay attention to what behaviors of mine left a bad taste in their mouth. What illicited disapproving responses and what questions caused them to feel more invested in the conversation. Basically, I never want anyone to feel like their time with me has been wasted so I did my best to make it enjoyable – even if they told me to my face that they didn’t find me as attractive in real life as opposed to my online pictures (another true story).

Whenever I tell a stranger that I have been on over one thousand first dates, I know what they think. That I must be some kind of “player” who uses women, manipulates their emotions and moves on to the next conquest – but that couldn’t be further from the truth. Because while I have had some unique experiences, I made sure to learn from each person. And as a symbolic thank you, I made sure that none of that time was wasted. Sure, the relationship may have not worked out, but few rarely do. And through those thousand plus dates, I wanted to make myself a better person through those interactions – so that one day, I could learn to make the people in my life, on my side, and on my arm happier and do my best to make them feel like I was a good investment. Even if I am more attractive online.

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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