Dating Confidently, And Why Good Teachers Know How To Do It.

*This is a repost from way back in the beginning of 2025.

In case you don’t know, I’m currently enjoying Cali, Colombia where I am taking Spanish classes for three hours a day, doing at least 90 minutes of private salsa classes, and doing my damndest to take gorgeous Latina women out on dates. As I was scrolling through the archive of my old posts, the title of this article couldn’t help but catch my eye. I reread it, and two things happened. One, I realized almost two years later my thoughts on dating had not changed. Two, I realized only 400 people have viewed it and it deserved another spot in the public eye. If you haven’t read it yet, I hope you have fun reading it as much I did re-reading it. ENJOY!

Imagine a girl waiting at the bar for a first date, and the guy walks in. We’ll call him guy #1. He doesn’t look perfect but he greets her with a smile. They start having a conversation. It’s clear he’s confident about who he is and what he wants. He loves what he does for a living. He makes easy eye contact. He also doesn’t mind sharing some of his quirks and vulnerabilities. He openly talks about his admittedly childish love for Pokemon cards. He makes fun of himself. When the conversation steers towards topics that they disagree about, he doesn’t dodge the questions; he lets her know his truthful opinion. He makes it clear he’s into her physically and he doesn’t hide his intentions.

Now imagine the scenario again, except this time the guy is drop dead gorgeous with stylish clothes and a perfect haircut. We’ll call him guy #2. Unfortunately, guy #2 can’t seem to meet her eye and it’s clear he’s nervous. When they talk, he just tries to agree with her. He attempts to tell jokes that fall flat…almost as if he read them from a dating book. When she asks him about his life he insists that everything is great, but he doesn’t delve into any detail. He’s super nice the entire date and never does anything impolite. He never expresses his sexual interest in her.

One of these guys is confident in himself and one of them is riddled with insecurities. Even though guy #1 is less physically attractive, my guess is he’s more fun overall and more likely to have a fantastic night. Guy #2 might have a fantastic night, but the moment he starts tiring of “trying to say the right thing,” the girl is going to grow frustrated with him.

If you’re asking yourself how does guy #1 just “be himself,” the answer is simple. It’s his attitude towards rejection. Let’s examine a classic soul-crushing moment that can happen to any guy - the girl turns away from a kiss. When this scenario happens to guy #1, instead of blaming the girl or mentally punishing himself for the way he acted, all he thinks to himself is, “bummer.” He simply recognizes that she’s not into him. It’s fine. He knows every girl is not going to magically like him. He’s cool with being himself regardless. Then he goes back to his awesome life and doesn’t let it bother him.

When guy #2 leans in for a kiss and he gets denied, his week is ruined, possibly his month. Best case scenario he goes back frustrated; questioning the way he acted and punishing himself for saying the wrong thing at the wrong time. It’s almost as if he’s analyzing a performance. Worst case scenario he calls the girl a whore, shit-talks her behind her back, and finds reasons why he never liked her in the first place.

Guy #1 just doesn’t give a fuck. He’s going to be who he is regardless of the circumstance. He’s going to go on the date, let his intentions be known, and hope she genuinely feels the same way by the end. His ability to not give a fuck is what makes him attractive.

Guy #2 gives all the fucks. He wants to say the right thing all the time. He’s nervous because he’s afraid of what she’ll think of him if he reveals his true self. Girls might consider his nervousness cute if he genuinely likes her but it’s rarely thought of as attractive. And if the guy is just trying to say the right thing in order to get laid, it’s crippling. Girls sniff out neediness faster than axe body spray.

When I think about Mr. Smith, I think about one of the biggest teacher assholes of all time. A minute late to practice meant a lap around the field while he yelled at you. A missed note often meant 25 pushups. If he was really pissed at your performance, he would have you stand next to him while your entire horn section did pushups. On such occasions he would yell at the horn section for not holding you accountable, and your peers would plot your demise. Kids, including myself, hated and feared him for this. He didn’t give a shit. The man simply did not care about your feelings.

He also built one of the greatest high school music programs in the country.

I learned music. I learned professionalism. I learned high standards. I learned leadership. I learned how to work. To this day it is the most effective organization I’ve ever been a part of, and it was run by a man who was never afraid of what his students thought about him.

Contrast that with Mr. Cerulean. He was my 6th grade math teacher. He was fun as hell.

Every day, I knew I could walk into math class and day dream as long as I wanted to. I didn’t really have to pay attention because the class was so easy. The man was all smiles all the time, and if a student felt bad, he would let them sleep in the back of class so they could “feel better.” One time the class average on a math quiz was around a 70, and everybody complained it was “too hard.” Mr. Cerulean gave a paper ball to a student and told him if he shot it in the garbage can everyone would get an extra 10 points on their quiz. Voilà! Miraculously, the entire class average jumped up an entire letter grade. That kid made the two foot shot into the garbage can like a champ. Kobe! We all cheered. Mr. Cerulean was the best.

Of course, I didn’t learn shit in that class.

After a year of not doing algebra, 7th grade came along and for the first time in my life I struggled in a math class. I had to go to extra help in my favorite subject. By the end of 6th grade, we all knew Mr. Cerulean was a useless teacher. He based his actions on getting the kids to like him, and to our detriment, all we did was take advantage. By the end of the year we were bereft of math skills and we viewed the man as a joke.

As weird as it sounds, I can’t help but make the connection between dating and teaching. Attractive people aren’t needy, they are confident. The same goes for effective teachers. They don’t need the approval of children to run their class. Attractive confident people and effective teachers don’t mind when someone doesn’t like them because they hold their own opinion of themselves in much higher regard. When a confident person gets rejected, they don’t feel bad about themselves. When an effective teacher upholds a grade when a kid is begging for extra credit, it’s because the teacher knows that’s what the student earned.

This doesn’t give these people a blank check to ignore whatever people say about them. Confident people are confident partially because they don’t mind admitting when they’re wrong. Effective teachers should listen to student criticism from time to time, it’s part of the process that keeps them effective. But, confident mates and high quality teachers know their own opinion of themselves comes first, and while they can and should listen to criticism, the opinions of others rarely shape their actions.

My final connection between confident dating and good teaching comes down to the word, “transactional.” Whenever I hear a dating horror story from girls, it usually follows this pattern. “I was having a nice date. He was good conversation and he paid for everything. However, when I got up to go he got annoyed because I refused to go to his car with him. It’s like he expected me…” That expectation part, that’s what leads girls towards the “ick.” The moment a guy expects sexual favors for his dating performance is the exact same moment a girl decides he isn’t worth pursuing, because all of his responses were trying to elicit a response from her. It’s not genuine. It’s needy and manipulative. It makes him a lesser man.

Letting your standards fall is a rookie teacher’s mistake. If a student acts in a way that the teacher doesn’t find acceptable and they don’t address the behavior immediately, that is the moment the teacher starts losing effectiveness. Usually they lower their standards because they don’t want to make a scene with the kid. They don’t want to hurt their feelings by calling them out. They don’t want the kid to get annoyed with them. They lower their standards in a transactional attempt to get the kids to like them. “Oh I’ll let it go this time…” When a teacher trades their standards in the hopes of being liked, they disempower themselves.

As a guy who both dates and teaches, I have a simple message for myself and anyone else in either camp. Uphold the values you hold dear despite other's’ opinions. Respond to all situations with the most honest version of yourself. Embrace being disliked. It leads to an attractive, effective life.

*5 years ago, I read Kevin Kelly’s article, “1000 True Fans.” The gist of it goes like this. Create a following of people who become fans of what you do. Be so damn good at what you do that people want to give you money so you continue doing it.

Here’s what I do. I teach, and I write stories about it.

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