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Years ago, when I was weak, needy, and contemptible, I would do anything to get girls to hook up with me, even if it was ethically questionable. I measured my self-worth by the number of women I slept with. I tried to make all of them believe they were individually special while I only really cared about their pussy.
In other words, I was a fuckboy. And the women I dated were mere objects to me. I proudly manipulated them into liking me, displayed them to gain status from my peers, especially if these women were exceptionally good-looking, and penetrated them only so I could feel better about myself — only so I could feel I still mattered.
And what do you fucking know — the catalyst that made me embark on this toxic and immature voyage was a simple breakup. I was about 17 when it hit me. However, to my surprise, the same thrilling, nauseating journey had a wholesome, even supremely practical, underlining.
Looking back at it now, I can discern 15 valuable dating lessons from the period. These are the sort of lessons that improved my entire love life — and that can improve yours as well.
Lesson #1: on vulnerability
The more you try to hide your flaws and imperfections, the more broken and ashamed you’ll feel. So, instead of emotionally inhibiting yourself, accept your flaws and imperfections, and stop hiding them. Live authentically. Humans are attracted to each other’s rough edges, after all.
That said, we can go overboard with this. So to be safe, at least for the first few dates with a person, avoid revealing deep, dark secrets. Likewise, don’t drone on about your ex or your breakup, even if the other person asks about it. And don’t trade fucking war stories. Pretty self-explanatory.
Lesson #2: on distractions
This lesson was a bitch to integrate. It goes like this: doubling down on dates to distract yourself from your pain won’t make you any happier. Even if you’re dating the smartest, most fun, and attractive people you can be around.
The only time dating will actually improve your mood is when you’re NOT using it as a means of running away from some emotional issue, or a past hurt, or trauma.
Lesson #3: on choices
The more people you date, the less each of those people and the experiences you share with them will matter to you. Now sometimes that leads to not being as fun or engaging on your date, which can completely ruin the vibe.
Therefore, don’t give yourself up to just about everyone. Be slow to date. Double down on those you have a powerful connection with; cut off the rest.
As cliche as it sounds, focus on quality over quantity.
Lesson #4: on diversification
Never make the person you’re dating the main source of your happiness and meaning. Diversify your sources of happiness and meaning instead.
Because if you mainly derive happiness and meaning from one thing, once that one thing fails or is taken away, you will end up in an existential crisis and feel like your life is meaningless.
However, if you can derive happiness and meaning from multiple sources, losing some of them won’t spiritually slaughter you. Because after losing some of the sources, you will always be able to fall back on the other ones.
Lesson #5: on insecurity
Breakups amplify our insecurities, and then those insecurities can sabotage our dates. In the past, I was often a bit jealous when my girlfriends hung out with their guy friends. But when I got into a breakup with those girlfriends, that insecurity got fucking intense, often making me cause unnecessary drama when I was meeting new people.
In the long term, let go of external validation. But in short, craft an “emotional battle plan” for when shit hits the fan. Something like, “When I feel insecure, I will do X instead of Y.” X being some healthy action like calling up a friend, and Y being some unhealthy action like going on a two-hour-long rant about how big of a bitch your ex was.
Lesson #6: on time
Time sure does heal breakup wounds — but it’s not a solution for every emotional problem. Sure, it helps us feel great and like ourselves again. It helps us be happy and content. It helps us reach a peaceful mental state. It helps us think less of our ex.
Only self-improvement can iron out those things. So throw yourself into it when heartbroken; don’t just wait for time to do its thing. Otherwise, you’ll leave a trail of decimated hearts behind you.
Lesson #7: on love
Always prioritize healthier values over love — values like trust, respect, honesty, loyalty, and empathy. Otherwise, you’ll eventually sacrifice your identity and self-respect in the name of love and get massively hurt as a result (see: the person who keeps coming back to a serial cheater because they oh-so love them).
As a great thinker once said, “Love is great. Love is necessary. Love is beautiful. But love is not enough.”
Lesson #8: on opportunities
The mindsets with which you pursue your dates will determine the caliber of dates you end up with.
Men who are shallow and objectify women end up attracting women who are shallow and objectify men. Women who treat themselves with no respect attract men who treat them with no respect. A person who values education and intelligence will end up with a date who also values education and intelligence. A person who hides their intentions and plays games will ultimately attract people who hide their intentions and play games.
The point of all this is to say that if you want better dating opportunities, you must improve yourself. By doing so, you’ll attract people with higher expectations and standards, and more compatible values, leading to more fulfilling relationships.
Lesson #9: on emotions
There are no good and bad emotions, only good and bad responses to emotions.
You can be angry at your ex and unnecessarily lash out on your date, or you can be angry at your ex, cancel the date, and go see a therapist instead. You can be triggered by something your date said and begin to behave like an ass, or you could not take it personally and genuinely try to understand where the other person is coming from.
Are they really an asshole, or was there simply miscommunication? Spoiler: it’s almost always just miscommunication. That, or your date is simply an idiot. Remember: most people are not evil, they’re just stupid.
Lesson #10: on numbers
You’re only compatible with a fraction of the people roaming this godforsaken planet. So going through rejection after rejection after rejection is completely normal when dating — and absolutely not a reason to lose hope.
Dating is, fundamentally, a numbers game. Get used to it. You’ve got to go through the “no’s” to get to the “yes’es.”
Lesson #11: on being single
Being single is far better than being in a shitty relationship.
A shitty relationship robs us of happiness, stymies personal growth, and erodes well-being and self-esteem, which could require years of therapy to then rebuild.
Meanwhile, being single allows you to be your full self, have complete freedom over your daily schedule, and invest in yourself however you see fit. It also means you’re not exposed to any sort of abuse, be it intentional or unintentional, that could leave you with unfortunate long-term consequences.
You might hate being single now, but the alternative could be way worse.
Lesson #12: on growth
Our failed relationships truly are a gift.
Without them, you wouldn’t have become the more resilient and mature person you are today; you wouldn’t have discovered the mystery of your own inner workings and emotional needs and what you’re actually looking for in a date; you wouldn’t even have learned the many essential skills that make a healthy, happy love life possible.
Be grateful for this stuff. A breakup is always an opportunity for growth, one you can leverage to dramatically enhance your dating life.
Lesson #13: on taking breaks
If you’re too tired of your dates not working out, know that you don’t have to continue dating. You can simply take a break.
It doesn’t mean you’re a failure, nor does it mean there’s something wrong with you. It’s a choice for you to make just because. Maybe now is not the time for you to be seeing someone. Maybe now is the time for you to be with yourself.
Chew on the idea.
Lesson #14: on chances
You always have more than one chance at love.
A simple “hello” could lead to a fun date. Then that fun date could lead to more fun dates. In a matter of months, you may end up in a beautiful relationship that lasts for a lifetime.
But if that doesn’t happen — if nothing lasting sprouts from your sexploits — who gives a fuck. You still have the ability to greet that other cute girl or guy you’ve been eyeing. And this time, you might build something lasting with them… Or you might not. But where’s the fun in knowing?
Lean into the uncertainty; don’t run away from it.
Lesson #15: on success
To succeed in dating, you must become someone who brings something to the table and who loves and values themselves. This is why I always say that dating advice (even relationship advice) is simply self-improvement in disguise.
If you don’t have an attractive identity, don’t have an enticing lifestyle, don’t have your emotional shit in order, and don’t value and love yourself — you’ll at some point sputter and stall like a broken car engine. And your love life will suck as a result.
In other words, creating success in dating starts with cultivating a great relationship with yourself. Hell, cultivating any great relationship starts with cultivating one of the same caliber with yourself.
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