There is an enormous difference between how I date in my 30s vs my 20s. I think the key distinguisher is I was a pure “chauffeur” back then, and now, I navigate the dating world through Mike Tyson’s eyes. I talk about being the chauffeur in many places so I won’t go into detail here. Just to say that being the chauffeur was my trauma response to growing up in a toxic environment. I believed that I was inferior to my partners. Respect was something I wanted but didn’t necessarily believe I deserved. I was exceptionally easily manipulated. I had terrible boundaries. To give you a quick summary.

Mike Tyson Represents the Opposite

Assertive, confident, direct, strong.

For starters… I was WAY less selective. If she was halfway cute, that was enough. I chased and chased and chased. I got invested in people way too quickly. I idealized them. I was more interested in getting their approval than protecting myself. Over time, most of my partners learned that I didn’t believe I deserved respect, so they didn’t feel obligated to give it to me.

I was seeing this Colombian girl in college. One night, she’s at my apartment. Just as she’s leaving around 10:30 to go home, I start feeling violently sick. It’s already clear that I’m probably going to throw up. I’m very nauseous. She leaves a little basin near my bed and goes home anyway.

Fast forward to 3 am, I’m vomiting, and I have diarrhea. I call her to ask her to get me to take me to the hospital. I didn’t have a car, and she lived with her mom. She used her car to get around when it was available.

She and her mom rented a room in the house to a guy who lived out of town. When he needed to for his job, he’d spend two or three nights per week there. So, he was parked behind her mom’s car in the driveway. She refused because coming to get me at night meant she might have to wake up their guest. She was basically like, “I’ll be fine…

So, I called 911 and told them to send an ambulance. I sat in the waiting room for 3 hours before being seen. All of that vomiting and diarrhea left me highly dehydrated. And my guts felt like they were shredded. I took the bus home. Two. Then, I crawled into bed, where I stayed for 3 days while I recovered.

My girlfriend felt very guilty that she didn’t come to get me. But that event permanently changed our relationship. And this was early on, too. This was probably the first moment I decided to stay in the relationship past its expiration date. Like… She’s already told me that she doesn’t care whether I live or die. Certainly not enough to save me. That my feelings do not matter, now, you may say that I don’t know what she felt — I can’t speak for her.

But here’s what I know:

Actions Speak Louder Than Words

If someone tells you through their actions that your well-being is less important than their need for their mother’s approval, you need to believe them.

I’ll give her some grace that I probably never considered, which was that her mother was a true dictator… so she was probably more scared about her mother’s wrath than abandoning me. But either way, the damage had been done. You aren’t supposed to come back after dropping the ball like that. Yet, I stayed.

I bitched and moaned about that event for years. Yet, I stayed. And I pretended it was just a mistake and that she would not make the same mistake again. Time went on. The memory faded. But she violated a vast boundary. She didn’t have my back in my time of need. I found out that night that I couldn’t count on her for my needs. She could expect help from me, but not the other way around.

This is an excellent example of what I mean when I say that self-hatred comes from self-abandonment. I stayed with someone who treated me like that. You bet your bottom dollar, and my self-respect took a hit. It’s so funny. At the beginning of that relationship, I thought I was the boss. But by the end, it was very clear that I wasn’t.

As the years passed and that episode faded into the background, I tried to tell myself that it was in the past and didn’t matter—or that I was overblowing it.

But, looking back, I see that I was wrong.

When you stay in a relationship where caring about you is optional, you pay a price sooner or later. It wasn’t just about me being abandoned but setting a precedent for myself. Once you allow specific behavior, it becomes infinitely more complex to turn around and say it’s not permitted later. That’s why I’m so vigilant about setting bad precedents. All you have to do is devalue me once so I can call it quits immediately. Or soon thereafter.

It’s one of those things I paid such a hefty price to learn these lessons that I don’t hesitate. I know what comes after tolerating bad treatment:

MORE BAD TREATMENT

There’s something about human nature. This is one of those instincts that I believe is primal. Because life has taught me that just about everybody responds similarly. People always look to you to see how you expect them to treat you. If you tell someone they can abandon you in your moment of need, you’ve set a terrible precedent in your relationship that will bite you later. The day will come when there may be a little incentive to abandon you — that person might choose to betray you because they know you’ll take it. This is human nature. The minute you tolerate being disrespected, devalued, abandoned… Everyone who sees that response instantly changes how they see you and what kind of treatment they believe you deserve.

That’s why it’s such a common trope of the new guy in prison to try to beat up the meanest guy in the yard to let everyone else know not to f**k with them. This is the law of the jungle. We are no better than chimpanzees.

My life has taught me that EVERY single time I have set a bad precedent like that in my romantic relationships, I’ve later regretted it because it’s almost impossible to enforce a boundary after you’ve let someone know that your boundaries don’t matter.

I have one client who once told me something profound. He said, “You have my full support until you start to devalue me. The minute that happens, everything changes.” I took this to heart. I used to hide my assertive side from people. I didn’t want people to think I was hostile or abusive.

But, these days, I am working on revealing my apex predator side as fast as possible — at the very first opportunity. This isn’t about yelling or being threatening… It’s not about talk; it’s about action. It’s about showing people what you will or won’t tolerate and being precise. One of the reasons I particularly love this boundary is because it’s easy for me to sort the masses into two groups:

SAFE people and UNSAFE people.

Easy. Safe people don’t try to hurt you or put you down. Not ever. Safe people respect your boundaries. They don’t try to f**k with you. They’re on your side consistently. They don’t undermine your judgment.

Unsafe people. These are the people who try to hurt you. Who put you down? Who criticizes you? Who thinks you’re small? You treat you like you’re a nobody. Who makes me feel like a chauffeur.

I’m hypervigilant about this last point. I’m not supposed to feel like a chauffeur around you. Not only that, but I also have very little patience for people who seem skeptical about my self-worth. If I see you trying to evaluate me? Looking all doubtful about me? No. Pass. Some people have no trouble seeing my value. I’m looking to spend my time around THOSE people.

If someone devalues you, you teach them that you deserve to be devalued. Furthermore, there’s no benefit to devaluing someone else. If you put down your partner in any way, you only hurt the connection. It only pushes them further away from you.

Therefore, there’s no place for devaluation in any of your relationships. Save the devaluing for your enemies ;-)

I have this hilarious beef with this one guy in the dance community. He’s always on the prowl for his next conquest, and he doesn’t like me because I think he views me as his main competitor.

Here’s the deal — I realized this guy was a fake friend one day. I don’t keep people around me who think it’s good enough to treat me well most of the time. He’s highly salty about me — mainly because once I identified him as an unsafe person, I started ONLY giving him my most Apex predator self. That’s the only version of me that he’s ever really known.

Which means I ignore him so profoundly. It’s deeper than you can even imagine. It’s very maddening when you won’t even acknowledge someone’s presence when they’re right in front of you, and friends are watching. I see him at almost every party, yet I haven’t spoken to him in years. It drives him up the wall.

He has so much unfettered rage for me. But, you know what?

I don’t accept people around me who think it’s okay to hurt me occasionally. Not even once in a while. Nope. You can’t make me. You don’t exist to me. If that means until the end of time, so be it. This boundary has served me well because literally every time I’ve ever thought about being friendly with him, I’ve instantly regretted it. I won’t accept people who are happy when I fall. Not once, or ever.

I just broke things off with a girl a couple of days ago. I’m most amused at the whole thing. There are so some people who, the moment you say you like them, they say, “Great, take a number. Fall in line.” And you look at the line, and it’s snaking out the door.

I Told Her Thanks But No Thanks

I noticed something exciting about this one. I was slipping into chauffeur mode. And just off the bat, I’m officially calling this a red flag in and of itself. If I start feeling like the chauffeur around you, that’s not a good sign. It could be because you’re emotionally unavailable. It could be because I’m feeling judged unfairly. It could be because I’m...

Dating in my 20s vs. my 30s