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)


For PUA newbies, here’s how strip clubs can help you

If you’re new to PUA and have a little money, you might be surprised to find that strip clubs are a great place to practice. You probably won’t get to fuck a stripper, but you can still learn a lot in a short period of time.

The Upside of Strip Clubs for Developing Your Game

You don’t have to worry about approaching. They generally will approach you. The best way to get a girl to come to your table is simply to make eye contact with her and smile. She will make a beeline your way unless she’s with another customer. In the real world you still will need to learn to approach, but by removing this initial source of anxiety you can focus on conversational tactics and not get stuck in your head thinking of an opener.

By going to strip clubs, you will get used to the experience of having conversations with very attractive women. Yes, these women are trying to game you. Don’t resent that. It’s their job. But they’re still people and would much prefer to have interesting conversations with a guy who doesn’t treat them like two-bit whores. A few nights ago I went to a strip club and the three hottest girls there kept coming back to hang out with me even though I gave them no money. One of them has even done cool favors for me like get me free tickets to concerts (her sister works at a local venue). I haven’t tried to sleep with any of them because they all have boyfriends (about which more below).

You can practice being cocky/funny and not worry about failing. It’s her job to seduce you, so she will put up with your lame jokes, awkward silences and stupid magic tricks. However, her body language will tell you whether it’s working or not. Again, you probably won’t take her home with you, but you can still look for IOIs and, conversely, when she’s turned off. Think of this as a chance to develop your calibration skills.

You can practice all the kino you want. Strippers are masters of kino. Observe the way she touches you and don’t be scared to touch her back. Don’t do anything crude like grab her ass. Touch her arm, play with her hands, let your legs intertwine, touch her hair while complimenting it, pull her close when she’s talking and you can’t hear what she’s saying (or even if you can).

You can develop good eye contact skills. Sometimes I go sit by the stage and wait for a girl to come dance for me. Instead of staring at her tits or ass, I lock eye contact and hold it the whole time. It’s actually really erotic. Some girls even blush.

Conversational Tips

  • Don’t talk about sex right away, or even at all. Most of the guys she talks to there are either super boring or immediately go for the dirty talk. She will put up with that because it’s her job, but she is turned off by it.
  • Don’t call her a “stripper.” Call her a “dancer.” She may still use that word, in which case it’s probably okay for you to use it too. But some girls are ashamed of what they do and don’t like to be reminded of it.
  • Don’t ask her about her job. Instead, practice deeper conversational topics like her passions, what her childhood was like (the stereotype about all strippers having shitty childhoods is BS), where she wants to travel to etc.
  • I’ve found that most strippers really do like to dance and often even have ballet training, so that’s a good topic. One girl I know danced professional ballet in New York. Another is training to audition for Cirque du Soleil.
  • At the start of a conversation, instead of asking “how are you?” ask “how’s your life?” It breaks them out of their usual pattern and they give much more thoughtful answers which lead to more interesting conversations.
  • Practice playful conversation. When girls ask me what I do I usually say I’m a CIA agent or an astronaut. When they ask me how old I am I say 74 (I’m in my mid forties).
  • Practice talking about yourself in an interesting way. Talk about your passions and in particular how they make you feel. For example, I like to ski, but instead of just sharing that fact I talk about the feeling I get of being “in the zone” when I’m tearing up a run. I use that to transition to asking her if she has anything that makes her feel that way.
  • Compliment her about something besides her looks. I try to find one of her passions. One stripper I know is a really talented painter. Another is a competitive ballroom dancer who competes in a different city every week. If nothing else, tell her she has a good energy about her.
  • If the topic of sex comes up, be original. Don’t tell her you want to fuck her. Instead ask her what’s the craziest thing she’s ever done, or tell her about an intense or funny sexual experience of your own. This past week I had a crazy three-way that ended on a really weird note. Last night at the strip club, instead of bragging or professing to be really good in bed, I talked in a cocky/funny way about how sometimes even an alpha male like me manages to fuck things up. The girls were eating it up.
  • (As an aside, some of them really are total horndogs who like to share TMI. Roll with it.)
  • Another playful way to talk about sex is to say you’re terrible at it. I say something like “I’m really bad in bed. I think it’s because I have terrible spatial skills and always forget what goes where, who’s supposed to be on top, where the TV remote is…” You can even joke about how small your dick is.
  • Many if not most of them will have boyfriends. Don’t be afraid to ask them about their relationships. You’ll be surprised by what they reveal. Never, ever put down her boyfriend in any way. She’ll put her shields up immediately.
  • Make it clear that you don’t judge her for what she does. I usually say something like “I love strippers. Not because they get naked, but because they have to earn every single dollar they take home. That’s not true of most jobs.”
  • (If you do judge strippers, do us all a favor and don’t go to strip clubs. We don’t need the negative energy there.)

Other Tips

  • Go early. I usually go around 9 pm. There aren’t many customers and a lot of girls are just sitting around bored. I also tend to go during the week when it’s not as busy. Sometimes the ratio is 3 women for every guy.
  • Another advantage of going early: hitting a strip club before going out to the bars is a good, no-risk way to get into state.
  • Don’t be a cheapskate. You don’t have to throw crazy make-it-rain money at the stage, but tip well.
  • If you want a lap dance, get one and don’t complain about the price. I personally don’t like lapdances, but sometimes I will just slip a girl a twenty and say “I know you’re working and I appreciate your spending time with me while on the clock. I’m not going to buy a lapdance from you, so if you want to work the room feel free.”
  • Tip the bartenders and waitresses well. I usually give one dollar per drink, even when they’re giving me free refills (more about that below).
  • I usually go into a club assuming I will spend $100 in a couple of hours, though I often spend much less. I don’t think of this as paying women for their time. I think of it as paying for entertainment.
  • Make friends with the bouncers and wait staff. This is a very useful skill to develop for the real world.
  • Don’t spend much time by the main stage. I only go there for a few minutes at a time to tip a specific girl I like, often one I’ve already talked to previously.
  • You won’t be attracted to every girl who hits you up. Tell her right away (with a friendly smile) that you won’t be buying a lap dance from her. Or if you’re there with a friend, tell her you haven’t seen him for a while and want to catch up. She’ll appreciate your not wasting her time.
  • Dress well. Even sex workers appreciate a man who has style.
  • Stay away from the really drunk girls. They have issues.
  • I personally don’t drink at strip clubs. I’m better able to observe the social dynamics when sober. Many clubs will give you free soft drinks if you tell them you’re the designated driver.

If you feel a real connection with a girl, tell her you’d like to get coffee with her sometime and ask for her number. If you’ve done all of the above well, many of them will give it to you. If she does, stop thinking of her as a stripper and just treat like any other girl you would try to date.

And if she doesn’t, think of it as practice at dealing with rejection. I’ve been rejected hundreds of times in real life. Getting to a place where you’re emotionally okay with rejection is one of the most important skills you can learn.

(Originally posted on Seddit)

Mining Craigslist

A while back I read this post by the web’s most popular asshole.

It gave me the idea to shamelessly steal that text and post it on my local Craigslist. I changed a couple details to make it seem local, but more or less verbatim. Check out this reply I got:

Hi there!
I have to say, I was blown away by this message to the entitled girl at the bar. You sound like an awesome, self respecting guy who is obviously aware of his surroundings. I’m also very impressed that you bought the other girl a drink instead, she seems like she deserved a drink much more than any girl who would come right out and ASK you to buy her a drink.

As a woman who has received her share of free drinks, I just have to say that the girl you’re referring to sounds like trash. Maybe that’s a little harsh, but it’s completely disrespectful of anyone to ask someone they just met to drop money on them. I personally know a lot of twits who go out for “free” almost every single night because they prey on guys who either honestly think they’re buying the girl’s attentions for the night -or- they have the money to spare on the off-chance that something might happen. In either case, I’m disgusted by this ridiculous mating ritual.

That said… maybe I’ll see you out there some night and treat you to a drink for proving that there are guys out there who stick to their values, simply because they respect themselves.

Thanks for the read,
Craigslist chick

I ended up getting probably a dozen messages along these lines. One girl (henceforth HB25) emailed me and we started going back & forth. Eventually we moved it to chat and it escalated pretty quickly.

She lives in a town about 45 minutes away, which as far as I’m concerned might as well be Siberia, so I figured we probably would not hook up because I didn’t want to drive all the way there. During the chat she mentioned that she’s a bit of an exhibitionist so I asked her to send me some pics. She sent me some cute, pg-rated self-photos. At some point I asked her when she was going to come pick me up and buy me a drink. She indicated she was up for it and I knew it was ON.

Here’s where it gets interesting and where my inner game paid off. She texted me to say that she was not going to get all tarted up. I wrote back simple “Wear something sexy.”

That’s when she started getting cold feet. She wrote back that she thought that was a bit inappropriate for me to say in anticipation of “just a drink,” and basically said she didn’t want to come, it was too soon, a little scary because I might be a serial killer blah blah blah.

IN MY AFC PAST I might have apologized and started chasing. Instead I wrote back:

“Whatevs. This from a chick that just sent me semi-nude pictures.”

She apologized and admitted she was flaking a bit. She also said she didn’t know why I was attracted to her in the first place, that we really had nothing in common. (Which was bull – she’s a writer and I dig writers and I could tell I’d have a great convo with her.) So I re-established rapport with:

“The idea is for us to have FUN. Sexy is fun.”

Re: why was I attracted, I said, “Um, maybe because you have an interesting mind? Remember what I said about writers?” (I had previously said that a) I like writers and b) writers are nuts as a general rule)

She wrote back: “Batshit crazy, I know.”

I wanted her to see herself as about to miss out on the best time of her life because of her own bullshit. So I said: “So this is really about you, not me.”

I told her that I was going to the bar regardless of whether she showed up and that maybe I’d see her there. At that point she called me. That released some of the tension and I teased her a little. She still said she wasn’t coming, that she was going to hook up with friends instead. She said she did want to see me so we talked about maybe hooking up Sunday or Monday. Then we hung up and I figured it was over. (She later told me that hearing my voice made me seem more real and sexy.)

Right about the same time I got a text from the 30-40 yo girls telling me where to meet them, so I thought, ok, I have a plan b. (I did hook up with them and it turned out one of them was a girl I dated a few times. LOL.)

On my way to the bar HB25 called me and said she was coming to see me. I was surprised but played it cool, like OF COURSE you’re coming to see me.

Once she showed up, I was pleasantly surprised at how hot she looked, and I could tell almost from the get-go that she was into me. We hit another bar briefly, where we started making out. At that point I said we can pretend to go to more bars or go to my place and she said my place.

Encountered a little LMR in bed, but I said I never have sex on the first date. “Really?” More foreplay and now we’re naked and I said I was going to put on a condom just to be safe. “Just to be safe? What’s that mean?” “It means just to be safe.” Thirty second later I was inside and she was screaming my name. We fucked a couple time during the night, woke up and fucked some more this AM around 8. Then I made some coffee and we hung out. She later told me she didn’t plan on having sex (they never do) and was positive she wouldn’t until 30 seconds before.

Here’s where it gets funny. I had previously scheduled a breakfast date with a chick I met through online dating. She texted me to confirm it and I said yeah, meet me at the local diner at 8:45. I had told HB25 that I would probably have to work today. I told her I was going to go meet my biz partners for breakfast but that she was welcome to hang out at my place and get some sleep.

So I went on the breakfast date and had a good time with her as well. During breakfast I got a text from HB25 that said “Just now…” and contained a close-up photo of her naughty bits. She was laying in my bed at home masturbating.

I nearly spit my coffee out all over my other date. Speaking of which, I took her to Best Buy because she wanted advice on buying a subnotebook computer. The dude at Best Buy ask what she needed the computer for and I said “Mainly watching porn. This chick can’t get enough porn.”

That sent her over the edge with laughter and we made lots of sexual jokes after that. I dropped her off and she texted me that I’m a lot of fun.

Then it was back home HB25 for another round. Took some more pics and even shot a little video. Good times. BTW She’s 25 which for most of you is old, but that’s 16 years younger than me, the biggest age difference I’ve ever closed. This morning as we were talking we realized she was born 5 days after my nephew. Gulp.

She also stroked my ego a lot. Told me I’m the best she’s ever had in bed (whatever, I was only her fifth and her second one-night stand) and kept telling me how hot I am. I try not to need validation from women, but it still feels good.

As a follow-up, she and I dated several more times. I told her on the second date that I didn’t actually write the CL ad. She thought it was pretty funny. We ended up splitting up because she wanted to be exclusive with me, but we’re still friends and chat frequently on gmail.

About to Drop Online Dating

I’m pretty close to dropping online dating, which is a big step for me. I’ve had a since — no shit — 1995 (I signed up back when the first 10,000 subscribers got a free account for life). I’ve used it off and on over the years with modest success and ultimately met  my now-ex-wife there.  After we decided to divorce, I started using it again and also a couple of others.

Since learning about Game, I made some changes to my profile to make it more alpha and used more of a flirty approach in my emails. It worked. I’ve met a lot of girls this way and even had two semi-serious relationships there.

However, as I’ve gotten better at meeting girls in real life, I’ve starting losing patience with online. Why? Let me count the reasons:

  1. Girls at dating site are usually looking for a long term, exclusive relationship. I’m not.
  2. The girls are generally not that attractive, except for the young ones
  3. The young ones generally do not respond to my messages. I suspect this is because they see my age in my profile and they automatically rule me out. (Girls I meet in real life regularly tell me I look five years younger than my real age.)
  4. Most of the girls’ profiles are pretty boring, so it’s a pain to think of something original to say.
  5. And since they are boring, most of them aren’t up to par for me anyway.
  6. The girls I like: sexy, good conversationalists and with a high sex drive, don’t seem to use online dating sites.
  7. The worst part: they can be just as flaky as in the real world. Too many times I’ve traded multiple emails with a girl only to have her flake out about meeting. Just yesterday I found myself chasing a girl because every time I suggested we meet, she came up with an excuse not to. I finally told her I was done and that if she wanted to meet it was her job to choose a date & time.

I’ll keep my profiles up, but I’m not going to spend as much time browsing and initiating contact.

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