The Playboy Progression

Question: How does one become a playboy without being a pretentious douchebag?

It was a fairly long journey for me. I’ve been divorced for about three years, but knew my marriage was ending for almost four. So let’s say 3.5 years since I started hitting on other women.

Here’s the emotional progression I went through:

  • Marriage ending phase: “I’m a loser. I can’t even hold a marriage together. I’ll never have children. I’m 40 years old. Who would ever want to date me.”
  • Rebound relationships phase: “OMG someone likes me! I’m in love. This is my chance to make things right. I better hold on to her.”
  • Rebound end: “OMG I really am just a loser.”
  • Started therapy. Stayed in it for about 18 months. (And I still go once or twice a year as a tuneup.)
  • Dating again, but more cautious. Assume that every girl I meet wants to have kids, get married and/or stay monogamous.
  • Get serious about my health. Start a bootcamp and discover that I’m more likely to stick to an exercise plan if it’s in a group. (Since then I’ve done Crossfit and a bunch of other classes. These days I’m really into power yoga.) Also start the slow carb diet.
  • Start attracting women, some of whom really do want to settle down. I realize that’s not what I need and start being honest about that. Some tears, but I’m still a “good guy” because I’m honest.
  • Start figuring out what I want out of life. I occasionally do nightlife stuff for fun, but I’m more of a fitness activity guy. So I start dance classes, do fitness workshops, occasionally do yoga.
  • Start dressing better. I already had decent fashion sense, but now I’m not afraid to dress a little flashy (not like Mystery or anything, more professional) and unbutton my shirt a little.
  • Start going to strip clubs more. At first I’m trying to pick up the girls (I read an e-book about gaming strippers). Now I just go because it’s fun.
  • Stop being ashamed of my sexuality. There is nothing wrong with wanting to fuck hot girls as long as you’re honest about it. Doesn’t mean I brag about it. (Likewise, I don’t brag about reading the New Yorker. It’s just something I like to do.) But if someone asks me what I’m looking for, I tell them. Though after you bang a few just for looks you start looking for more. I want hot, smart girls and will sacrifice looks for smarts.
  • Redefine my definition of “adventure.” My therapist was a big help in this. I used to think it meant being Indiana Jones or some other archetype – the hero who gets the girl in the end. But if you look up the definition of adventure, you’ll find that it basically means taking a risk. Sometimes risks don’t pay off, but they will never pay off if you don’t take a risk in the first place. So I start thinking of every social risk as a potential adventure. Mind you, I still get approach anxiety and shy away from ego pain at times; I’m not 100% perfect. But this mindset has helped me a lot in just about every phase of my life, professional as well as social.
  • I also ask myself, “is [activity xyz] scary?” If so, I’m probably doing it right. (I don’t take existential risks like, say, climbing Mt. Everest. Those kinds of things don’t interest me.)
  • Start thinking of myself as a catch and a giver of value. Among other things, I’ve decided that my life purpose is to 1) help people in their careers and 2) help people feel good about themselves. So I’ve been doing more and more mentoring. And if I see someone is dressed well, or has a good personality, I compliment them on that. No agenda except to get a smile and “thanks.”
  • Somewhere in there I realized that most women will not want to sleep with me, and become comfortable with that. Sometimes it’s logistics, often it’s because they’re married or otherwise occupied, often it’s because I’m not their type. That’s okay. The goal is to find someone who likes the real me as much as like the real her, and not worry about mismatches.
  • As part of that, start assuming intimacy with whoever I talk to. Be vulnerable, which invites intimacy in return. Sometimes it doesn’t work but who cares? Most of the time it’s fantastic. I was in NYC during hurricane Sandy and met a lot of interesting people simply by saying “hi.” Ended up having a devil’s three way that ended up strangely, but since then I’ve reconnected with the girl and she may end up helping me in my career. But even if I never spoke to her again I’d have a good memory to cherish, plus I learned a little in the process.
  • Which leads to the realization that life is something you do, not a goal to have a happy ending. My goal is to wake up every morning and have a great day. That’s it. It may involve progress at work, an adventure, or just surfing Reddit. As long as I maintain healthy habits (exercise, diet, getting out from time to time), it’s okay to dick around every once in a while.
  • Relatedly, realize that if everything dear to me was taken away from me — material possessions, family relationships, my work etc — that would be okay. It would be a setback, but the process of building an entirely new life would be a fun adventure. (Got this from Man’s Search for Meaning. Victor Frankl survived the Holocaust partly because of this mindset.) This is where the importance of giving value is important. If I pursue my life purpose of helping people and making people feel good about themselves (again, while maintaining healthy habits), everything else will take care of itself.

All of these may look like one thing on the outside, but are something else on the inside. The most important question I ask myself before doing anything is, “is this what I want, or am I trying to impress someone?” If the latter, I re-evaluate my decision.

It’s important to emphasize that therapy was a big help for me in all this. If you’re confused or not sure what to do next, consider therapy. Try multiple therapists until you find one you like.

Also, I’ve suffered from depression off and on since my twenties. I take Zoloft and it’s been fantastic for me (I tried several other medications first). I don’t know how I would feel if I went off it. But I don’t care either. I’ll probably try going off it in the next year, but if I fall back into depression then I will start again. There is nothing wrong with medication. The only thing wrong is thinking life has to be a struggle and you’re a lesser person for relying on meds.

(Originally posted on Seddit)


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