How To Be Cool

How To Be Cool

She was one of the first strangers I met from the internet. I’m pretty sure we found each other on AOL personals or whatever it was that was at the genesis of online dating. We chatted over AIM for a few weeks both playing coy and slightly reluctant to ask each other out. Keep in mind, these were the days when everyone was 100% positive that if you met someone in real life that you met from a chatroom they were absolutely going to be an axe murderer. But eventually her magic combination of charm, intelligence, and sass worked it’s magic on me and I found myself driving the 45 minutes into Chicago from the suburbs.

We met at a cozy little coffeehouse with a patio. She was more attractive than her pictures and I was enamored by the way she kept shifting her hair out of her eyes like it was a slow-motion scene from an 80’s movie. By all social standards, she was attractive. Hot. And she moved like she knew it. I sat there listening to her name-drop all the D list celebs she claimed to know but I let it slide because I felt like she was ridiculously sexy and I was just excited to be sitting across from someone so far out of my league. So I believed.

We finished our coffee and hopped in my car and I drove and showed around the city pointing out Al Capone landmarks and movie filming locations. She seemed bored, almost bothered by my enthusiasm.

“And here’s where they filmed that part in Ferris Bueller… ”
“Eh, can we go somewhere?” She snipped.
“Well, where would you like to go?”
“Ugh,” She shook her head. “I don’t know, just let’s do something cool.”
I felt a little defeated and the pitch in my voice lowered.
Innocently, I asked, “I, well, what do you think would be cool to do?”
“Isn’t this YOUR city? Don’t you know where cool people are hanging out?”

It was one of those moments where you know there is just the right comeback but you won’t think of it until you’re lying in bed just about to close your eyes for the night. I was taken aback. I watched as she stared out the window, longing for a better time.

“Well, I think it’s getting late and I want to get back home and it’s going to be a long drive.”
“Well then, can you drop me off at this bar I heard of?”

We pulled up out front, she reached over and gave me a quick half hug – the kind reserved for irritated teenagers who are far too cool to be hugging their mom in front of people. She closed the door and didn’t look back. My first online date and I left feeling bad about myself.

A week went by and I figured I would never hear from her again, that was, until my phone rang and she asked when we were hanging out again. Immediately, all of her ugly behavior evaporated and I agreed to meet up again. Probably a little too enthusiastically because it was met with a, “Ew, clam down.” I planned it out this time. I wasn’t going to be be seen as “uncool” again. She was new to the city and was into similar music and social circles but didn’t know anyone in town. I picked her up on a Monday evening and brought along a couple friends of mine. We drove to our favorite restaurant and I ordered what seemed like half the menu because I wanted her to try so many things. Then we drove to a secret spot where you can watch the dolphins swim alone at night at the aquarium. Then I took her to Rock-n-bowl. Now, this wasn’t your average bowling alley. In it’s era, it had become one of the most sought after places to hang out on a Monday night in the entire city. When you walked in, it was packed with every subculture weirdo you could imagine and we were greeted like royalty. Lanes would be booked for hours by bands like Bad Religion, Alkaline Trio, Good Charlotte, and uh, Nickelback. Anyway. We walked in and I introduced her to security guards and door men and bartenders and DJs to Chicago’s most eclectic clubs. I took it upon myself to network for her. So she could make friends.

We got a couple drinks and sat down at a table. Eventually we had a little time alone and I shouted over the music, “So what do you think?”
Her face grimaced, “Uh, well, when are we going to DO something?”
I was in outright shock.
“Do something?!” Confused, I shook my head.
“Yeah, like, uh, can we get out of here and go do something cool?”
My friend returned to the table before I could respond and I gave him a look that said, This. Chick. Sucks.
“Hey man, I’ll be back.” I said to him, “I’m taking her home.”
She looked up surprised, “Home?”
“Yep,” I said, standing up. “I feel like you’re not having a good time so I just think it’s for the best.”
We walked out to the car and I was fuming. All of the time, money, and energy I had invested. I felt fooled. Conned. But worst of all, unappreciated. I did my best to hold it together but it was clear that I was not happy with her whatsoever. She didn’t ask what was wrong. She didn’t ask why I wanted to leave so abruptly. She just sat there in silence for a few minutes then asked if I would drop her off at another bar. I told her that we were almost back to her building and I would just drop her off there. She let out a irritated and intentionally heavy sigh. We pulled up to her building, she walked out, slammed the door, and I never spoke to her again.

I went back to my friends and vented about how disappointed I was with her and her behavior. A few mentioned that I handled it as well as I could, considering the circumstances. Other friends weren’t so nice. But the night continued and we all drank Shirley Temples and listened to Misfits songs blast over the speakers and had fun and watched our friends bowl until 1am.

I distinctly remember that car ride home. Driving down 55 and listening to Saves The Day, I thought about how defeated she made me feel. Like I should have been ashamed for trying so hard. And in retrospect, maybe I should a little – if only because my efforts were wasted on someone who couldn’t even muster a simple “thank you.” But we will all have unappreciative people in our lives no matter what we do and no one will ever treat us with the respect we believe we deserve. I can handle that. What I couldn’t handle, was that she made me question my validity – because I am cool, dammit. I mean, I might not be the most handsome or the most intelligent or have the nicest body or the biggest bank account, but the one thing I do have is that I would like to think that I am fun to be around. I have interesting things to say, I can take a joke, I can tell a joke, I’m a good listener, I have read a couple books, and gained insight by traveling to different countries and exploring different cultures – so yeah, you know what. I AM cool.

And what I realized, as I gripped that wheel driving down the expressway, was that if you wait around for validation of your character, you will live a very frustrated life. Throughout the course of your time here, very few people will ever acknowledge and appreciate the depth of your character and the ones that will, probably want something from you.

Who we are is a collection of what we give to the world. Our honesty, intelligence, humor – our ability to make someone feel loved and appreciated, our loyalty to back up and be there for our friends, our concern for others happiness, our knowledge we share with others without being condescending, keeping people intrigued, entertained, smiling. Our calm and resilient demeanor that only comes from a deep rooted confidence in knowing that irrational, vapid, and selfish people can not and will not shake the way we feel about ourselves or obscure what we see in the mirror. These are the attributes that make up our character. And these are the things that make us cool.

And while I still feel the same social pressures, I do it a little differently now. I am a work in progress – always trying to be my own validation. Which is tough, because I hold myself to higher standards. But it’s that toughness, that fight, that burning desire to be a little better of a person than I was the day before. That is what makes me who I am. A tempered and confident person who does his best to make his corner of the world a little shinier for others.

And if I would have known that back when I sat down for that latte, things would have gone much differently that evening.

How To Be Cool

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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