4 Powerful Lessons from 1.2 Decades of Relationship Mistakes

Over the years, I’ve made thousands of mistakes in romantic relationships.

These mistakes have taken a toll on my partners and me, leading to sleepless nights, existential angst, and overwhelming feelings of deficiency. Since I don’t enjoy experiencing pain or causing it for others, I’ve tried to learn from my mistakes and move forward a better man.

In this piece, I’m going to explore four valuable lessons I’ve learned through my many relationship mistakes. 

Before I begin, I want to admit that I’m not proud of everything that I’ve done or the person who I’ve been. Especially in my youth, I operated very selfishly in my relationships. While I’d love to blame everything on being young and dumb, that’s not a good excuse. We can only improve to the extent that we take responsibility for our mistakes and do the inner work required to grow.

If you take anything from this article, it’s the following:

Take responsibility for your mistakes, reflect honestly about why you made each mistake, and figure out how you can do better in the future.

If you do this, you’ll be ahead of most people.

Let’s get to lesson number one – what you should do when you make a mistake.

What to do when you fuck up in a relationship

I’ve fucked up in countless ways in my relationships. From forgetting to pick up groceries to being a self-centered asshole, time and time again, I’ve said or done the wrong thing. Sometimes, I agree that I’ve made a mistake; other times, I don’t. Some mistakes are big; others are small. The point is that my actions hurt my partner.

In the relationships of my late teens and early twenties, if my partner felt hurt, I would try to debate whether or not my partner was justified in her hurt. I’d try to understand if the source of her pain was the result of something terrible that I did, or if she was falling victim to a cognitive bias, irrational thinking, or faulty memory selection.

It took me years to learn that applying psychology and life coaching to emotionally charged situations with your partner is a losing strategy.

Even if you prove that your partner is being irrational or letting a cognitive bias drive her decision making, you still lose. You lose because in attributing the hurt you caused to your partner’s irrationality or faulty human operating system, you’re invalidating her pain. And when you invalidate someone or don’t allow them to feel heard, you’re causing even more pain.

Instead of figuring out who’s “right,” I’ve learned to quiet my inner voice and take responsibility for the situation. Taking responsibility for the pain you’ve caused is the first step to healing. It can be as simple as, “You’re hurt, and I’m sorry for that, I’d like to work through this together.”

So if you’ve caused pain to another person, first take responsibility for causing the pain. Stop being defensive. Stop worrying about who’s “right.” Stop feeling attached. Once you’ve quieted your ego and taken responsibility, take these three steps:

1. Listen deeply to understand your partner’s perspective. Ask your partner to explain to you what hurt them. Especially when you disagree with something or see it differently, take the time to listen without judgment. It’s essential that your partner feels heard and that you understand her source of pain. It’s often not what you think.
2. Sincerely apologize. Once you understand why your partner is hurt, it’s time to apologize. You never wanted to cause your partner pain, and you certainly don’t want to do it again. Say sorry in a genuine way, and commit to being better in the future.
3. Learn from your mistake and show it in your actions. Talking about learning from your mistakes and becoming a better person is a start, but you need to give your words meaning through action. If your behavior hasn’t changed, your words mean nothing.

If you use this approach when you hurt your partner, you will end up with better outcomes. There will be times when your partner doesn’t want to work with you. If that is the case, then that’s on her. You can’t control her response.

Finally, remember that the healing process takes time. If you do something that damages the trust in your relationship, it may take months or years to rebuild a solid foundation.

Don’t cheat (or let yourself get cheated on)

In 2006, my first love cheated on me. She broke my heart, and I spent Christmas Eve crying in a small room while my step-uncle repeatedly told me to “stop being a pussy and suck it up.” As you might expect, this experience scarred my adolescent soul.

For nearly a decade after the event, I struggled to trust the women I dated. I thought that it was only a matter of time before they would cheat on me and crush my soul. And while it’s difficult to admit, my lack of trust manifested in destructive ways.

In an attempt to protect myself from the hurt of being cheated on, I acted unfaithfully at times. While I didn’t recognize it until years later, my subconscious fell victim to the following line of thinking: 

If I cheat first, then I’m safe from being hurt. If my partner later cheats on me, that’s just an equalizing act that makes up for my transgression.

While I wasn’t fully conscious of this fucked up line of thinking at the time, looking back, it was the strongest driver of my infidelities. My actions were wrong, and it took me years to understand and reshape the values and stories driving my behavior. In that process of honest reflection and re-examining my values, I learned two things that helped me understand why people cheat and why you shouldn’t cheat:

Cheating can be infinitely destructive. Cheating extends beyond the event itself; its adverse effects can ripple on for decades. Not only does cheating erode the moral fabric of the relationship in which it occurs, but it can undermine a person’s trust in all people and relationships. And that erosion of trust can last for years, spreading chaos, pain, and suffering to other people.

Cheating is a values problem. If someone cheats, it’s because they are valuing something other than the relationship. It might be a desire for power, validation through sex, or an unconscious action to protect themselves from being hurt. Whatever the reason, the cheater is prioritizing something over fostering a healthy and trusting relationship.

Most people agree that cheating is wrong, yet 20 to 25 percent of people who are married cheat on their partners. It’s not worth it, and it never will be. 

If you find yourself cheating across multiple relationships, it’s worth understanding how your actions can cause tsunamis of pain, re-examining your values, and considering alternative lifestyles that may not confine you to the constraints of monogamy.

If you’re a nerd, be a nerd

I love reading and writing. I love sitting alone and not talking to anyone for hours. I love getting excited about new ways of understanding and talking about the human experience.

Weirded out? Good. 

Many people hate the things I love. And guess what? That’s okay! 

What’s not okay is if I subvert who I am to be someone that I think another person wants me to be. You can’t maintain a healthy relationship on those terms, and as cliche as it sounds, you have to learn to be yourself around your partner. Otherwise, you’ll wake up one day filled resentment about not becoming the person you always wanted to be.

“About all you can do in life is be who you are. Some people will love you for you. Most will love you for what you can do for them, and some won’t like you at all.” – Rita Mae Brown

To have a healthy relationship, you need to get comfortable with all of your wacky thoughts, behaviors, fantasies, and beliefs. Accepting yourself doesn’t mean that you should stop pursuing personal growth. If you have destructive qualities or behaviors, tackle those issues head-on. But don’t stay in a relationship if your partner doesn’t accept you.

Sometimes, the timing isn’t right

During my twenties, I’ve broken off multiple good relationships. I didn’t leave these relationships because they were terrible or even mediocre, I left them so that I could travel the world and embark on an uncertain path without restrictions. I choose freedom and personal growth over my relationship.

People like to say that “if you want to make it work, you’ll make it work.” I think this is half-baked advice. Sometimes, you do want to make it work, but the costs are too high. To make it work, you might have to stunt parts of yourself, at least in the short-term, and you need to decide if that’s worth it. For some people, it’s worth it. For others, it’s not.

While you can’t predict the future, you can ask yourself hard questions and play out different scenarios. For example, if you need to set aside your dream to travel the world or pass up on a life-changing career opportunity to make it work with your partner, how will you feel if that relationship doesn’t work out? Will you be able to sleep at night ten years down the road?

Don’t let your hormones or partner make this decision for you. Sometimes, the answer is that you won’t be able to sleep at night in the downside scenario, and instead of risking that, you decide to minimize your future regrets and leave the relationship.

Other times, you may have found someone amazing, but they’re on a different growth trajectory. For example, perhaps you need to mature in specific ways before being able to maintain a healthy relationship. Or maybe she needs to have more professional success to be in the right headspace to commit in the way that the relationship requires. In these cases of diverging growth trajectories, it’s entirely possible that instead of “making it work,” the best thing to do is to leave the relationship and see how the future plays out.

These are all difficult decisions, but they’re incredibly important. Especially in your twenties, I think it’s worth considering whether or not you should continue in a relationship that prevents you from growing in the ways that you want. 

Learn from your mistakes

When you fuck up, it’s easy to blame the other person. It’s more comfortable to sweep your mistakes under the carpet and move on to the next person. But if you do this, you’re going to repeat the same mistakes, over and over. And one day, you’ll wake up single, fat, balding, and confused about why none of your relationships worked out.

Instead of avoiding responsibility for your relationship failures, take the noble path of confronting your demons. Learn something from all the nights of pain, anger, distress, tears, guilt, and frustration. When you’re stable enough, look in the mirror and say, “Wow, I fucked up. What happened, and how can I prevent this from happening in the future?

It’s not easy, but it’s worth the effort.