What's the Endgame for a Playboy? | Girls Chase

What's the Endgame for a Playboy?

Chase Amante

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playboy endgame
You won't stay young, wild, and energetic forever. So what happens to the old playboy when age catches up to him? Does he just fade away?

Under my article "Male vs. Female Mating Motivations Laid Bare", a reader comments:

hard question to ask, but it just seems having children or getting married is a no win situation, if she wants to she can put you on child support or divorce you when she feels like it. with that being said is there a way to have kids and not be put on child support? is there a way to not have kids as an older man and not get looked at as weird? I'm actually really interested in the not paying child support part. what's your plan for yourself Chase logically with this stuff? do you plan to have kids and get married? or just have kids? I liked to know your process of what you think older you would do with women.

I feel like making an "Old players never die, they just..." joke, but can't think of a good one.

"They just NEXT away"?

Nah, too obscure.

Well, anyway. The "what's the endgame?" question is a valid one for the modern playboy.

I'm going to skip the child support one, because, well, it's not realistic for most guys. Children are costly, and someone has to pay for them. Women usually can't pay for them themselves (some rich women excepted, but there's problems with targeting rich women to sire offspring with, then peace out, that I won't go into here). If the father won't/can't pay, the burden then falls to society, simply so the child doesn't die or end up scrounging for scraps on the street like what you see in less developed countries. So most societies have laws mandating fathers pay for their own children, to avoid having it come out of everyone else's pockets. There's no way to get around that in most developed societies without just being a straight-up dead-beat dad who knocks chicks up then runs away and hides so they can't collect child support, then runs away and hides again if he's found and hit with back child support payments. Which I guess you could do, but it's trash behavior, and you're hopefully on this site to learn how to improve your life, rather than lead a trashier one.

The child support question aside, that "what's the endgame?" question, now that's an interesting question.

Because, well... it isn't clear what the endgame for most men IS any longer.

Chase AmanteAbout the Author: Chase Amante

Chase woke up one day in 2004 tired of being alone. So, he set to work and read every book he could find, studied every teacher he could meet, and talked to every girl he could talk to to figure out dating. After four years, scads of lays, and many great girlfriends (plus plenty of failures along the way), he launched this website. He will teach you everything he knows about girls in one single program in his One Date System.



Risenin2019's picture

Grew up repressed up until about my early 20s, even had to go to a local school due to overbearing parenting. I have to say this is eye opening because I grew up in one of the most fake, morally self-righteous, two-faced, and goody two-shoe part of the US, the good ol deep south. 

Confused me too, it seems like the way American society works is:

High school -> Have sex and explore the other sex more

College -> Go wild and have tons of sex

Right out of college -> Okay settle down, you're nearing your end now

25 or so -> Have kids and a marriage

It made no sense to me either, you're finally rich when it comes to finances and have more freedom now if you did it right. They say men peak in their 30s or so, well why are Dan Bilzerians so rare? Why is hedonism and sleeping around with lots of women only acceptable in college and high school, why not in the "real world"? More men, especially those who are now finally hitting their prime and didn't have the golden spoon in their mouth like some rich frat guy did, should want to sow their wild oats but why is this idea so unheard of?

I then realized that the "social pressure" you talk about is society having to pander to the losers and the norm. The ugly chick who has no man or is very limited in her options or the average guy who doesn't have what it takes to make it in the game, society has to at some degree pander to him. Marriage was invented to keep the losers who would otherwise not even be reproducing calm so disaster does not strike (large scale Eliot Rodgers). 

What really gets me in the player path is the lack of camraderie with fellow men who also pursue that path that you do not get with age.  A guy who peaks in college can get it with his bros but a guy who peaks in his 30s is heading into it as a lone ranger, only at the envy of most men who made nothing of their lives and want him to fail. I have missed out on too much to consider monogamy and that chip on my shoulder will always be there. Good shit though Chase!

Benjamin's picture

I was intrigued to know that you did one sided monogamy relationships. I learned hector did them and I figured you probably did them too since you are a man of great influence and made yourself desireable to women. How many lays and relationship experience would a man need to have to realisticly be able to pull off a one sided relationship with a moderately attractive woman? Also were you financially stable when you had those kinds of relationships? Or can you still pull off the broke lover? Social dynamics discussed on this site is very forbidden to talk about in society,but how do you resist the urge to do this when everybody around you talks gibberish and to whom could you discuss this with who aren't initiated? Any man who aspires to improve themselves with women through seduction is completely alone and has no one to support him. It just sucks. Obviously you were able to pull it off,but it's still very easy to be discouraged. My friends are not people I could convert to believe in this type of stuff and it sucks because they are good guys.

Curious as well's picture

I wanted to ask this same question and wanted the email notification lol

Naye's picture

"How many lays and relationship experience?"

Dude I pulled this off with just 3 lays and 0 relationship experience. Asking that question just shows you imposing limitations on yourself ;)

"Were you financially stable?"

Was broke and living with my parents.


Numbers are not enough to tell you if you are ready or not. Personally I wasn't sure if I could pull it off or not but I went for it anyway.That relationship lasted just under 3 years. Push yourself outside of your comfort zone and you'll be surprised at what you can pull off.

SZ's picture

Really good article, the thing I believe, everything gets old, commitment and being single, both get boring after a while, but being committed is easier because you don't have to keep going out.

1. what do you think of the case if you go longer than the 2 year drop? a girl I was seeing still contacts me to this day and I've known her about 5 years and we fucked for 3. there was a drop during the second year, but that was because of me, I tried to distance myself from her while she still chased me and still does to this day. so I stopped talking to her after the 3rd year, but she still wanted to be with me even after I didn't talk to her for some time.

maybe the situation was different? we weren't really too public, never met her fam, and we only saw each other for a few days a week.

so why do you think that lasted so long? do you think if she's chasing commitment that it goes past the 2 year drop, instead of actually giving her the relationship and not stepping up the relationship with kids or marriage like a normal 2 year drop? does her wanting the basic commitment make it last longer?

2. what do you feel about guys who are repressed and have to learn game way later? what if they did what society said and settled down kind of young, but later on are really sad they didn't sleep with more women, not they are older and maybe still married or divorced, but they never had the success and now are very bitter because of it. do they just end up being single and learn how to get women? wouldn't it be that much harder because of age? what if he wants to make up for lost time?

3. you said that men who have slept around with a good amount of women never really settle down, so do these guys still cheat on their wives? do these guys really sleep around at 60+ years old?

4. to me in this day and age every girl is different, do you really think it's wise to really settle down? I'm not saying this like a young boy says he doesn't want to settle down, but I'm talking from the view of dealing with the drama that comes with it and if you decide to split? what if modern women have made you too bitter?

Will KZ's picture

Great article. Originally I misread the title and thought it said "whats the endgame for Playboy", which seems to have the endgame plan of becoming super progressive and lecturing men on assorted BS, much like GQ...perhaps all men's magazines will soon become Jezebel light.

But your actual article was far more interesting. I remember the Tiger Woods thing putting me off mainstream media when I saw the only mainstream people saying anything close to the truth were a few comedians while everyone else, was shocked, shocked to find that a famous, athletic man nicknamed Tiger, worth billions (or close), might dare seek out extramarital flings. 

I wonder what my endgame will be. In my early 30s now, focused more on money than women. Wonder how I'll feel in my 40s whatever path I take.

Lao Che's picture

being single and childless as you head into your mid-forties is a bad place to be. the ride doesn't last forever and you'd better figure out where to get off before you get thrown off. family is EVERYTHING, whether you think so right now or not



i've had to start telling people i'm divorced, just so they don't think i'm gay or a weirdo. it's just easier. 

how old is Chase?

Mr.Rob's picture

Every once in a blue moon they come around. Bravo! 

Really good points on the "current state of affairs of mistresses and one sided monogomy". I read JFK's biography and that guy had pussy delivered to him on a daily basis like rock star status. The meds he was on for his pretty severe addisons disease compounded his sex drive through the roof (not a bad side effect lol) and was quoted "if I go 3 days without a woman I get major anxiety and can't sleep". His staff and secret service were constantly supplying him women and keeping steady tabs on all his mistresses to prevent a scandal from what I gather.

Interesting stuff, but my gosh what a pain in the dick to be a celebrity or powerful man married in today's social media/cellphone age where its even harder to keep things private and under wraps!! I'm sure it makes some powerful men want say "to hell with it" and go start a cult! 

If you end up weighing in on the comment section here I'd be curious to get your toughts on "mistress game" (if your willing to give away those secrets that is [which Im sure you have ascertained from 2nd hand sources only ;) ... Namely how do you run a mistress relationship? Is it basically a run the same way as a casual FWB or do you have a mini monogamous relationship with her. Thing is I know successful ppl w/ mistresses having long term (1 year +) relationships which kinda defies the casual relationship 3-4 month typical thing.

So eh changing tack here... what would you "guess" ;), is the best way to run mistress game? Is it run the same way as a FWB/Casual relationship or "would you imagine" there are certain intricacies to keeping her on board and cool with being a side chick. I guess there's probably an inherent value in being sexually involved with a powerful man even if he'll never commit to more than just fucking her (she gets his access to his seed).

I know many famous men had mistresses that lasted years long in duration which defies the typical 3-5 month long casual relationship expiration, so is this a different beast? 

Anyway awesome article boss man.



Mr.Rob's picture

Eh I sent the original comment off without fixing the Edit I made there. Sorry for the confusing paragraphs at the end there. 

SZ's picture

Another thing Chase,

I wanted your opinion on this.

1. When should a guy get married? or should he even get married? but if he should get married, what do you think Is the best situation?

should a guy marry young with no skillet with women because of society norms? I ask young because the older you get the harder it is to get married to younger women who have their stuff together with low baggage. the man would also have to get good skills with women to get younger women as well.

or should he wait until he gets to a certain skill level with women before getting married? and how many partners should he be at?

2. what does a guy do while married? does he just not care about other women anymore? does he just let his skillset fade? what is the endgame for a married man? it sounds so boring to not not have attractive girls all throughout your life.

3. this kind of adds in to the 2nd question. what are real old guys supposed to do whether married or single? I'm talking 60+ like should they just quit pick up all together if they're single? or should they just really not care about seduction or being in shape (let themselves go), be a sugar daddy, pick up 40 year old women? lol. and what should they do if they're married and that old? like what's your opinion on what real older men should do whether they're single or not when it comes to all types of self improvement?

SZ's picture

Chase, could you elaborate more on how playboys never fully settle down?

you said they really can't fully be faithful.

and I'm guessing you mean this well into age.

so how do these guys do this without getting caught and divorced or whatever?

how does that while scenario play out with finding the girls, dating, sleeping, etc. while being really old and maybe married?


Anonym's picture

Hi Chase,

Thanks for an interesting article. I have a few notes here:

  1. Ad powerful men always having mistresses and being polygamous. Of course many powerful men live this way. But there are examples of powerful men living monogamous or non-sexual life because of different reasons: religion (f.e. the popes – at least some of them), focus on work (Nikola Tesla), repressed sexuality (Cecil Rhodes, Adolf Hitler), introversion/awkwardness/shyness/possible autism (Bill Gates, Lionel Messi). For example, Victorian public schools trained young English men to repress their sexuality and many of otherwise hypermasculine builders of the British Empire were not sexually active. Probably some other deeply religious powerful men were disciplined enough not to live in polygamy. Etc.
  1. I am surprised that in your comparison difference of the West and the other parts of the world you do not mention Christianity (and Judaism) as a factor of cultural dominance of monogamy. If you are practicing Christian, you are allowed to have sex only in marriage and you can marry only one woman. If you follow the rules, you have to be monogamous. Traditional Christian (or secular) Western family is based on marriage between one man and one woman who have children together. Mutual monogamy seems like natural and logical implication (or precondition) of this model. Cultural influence of the West to a big extent overlap with spread of Christianity, though in some regions there is syncretism with local cultures and therefore more visible polygamy. Moreover, if ratio of men and women in polupation is balanced, then monogamy is better since more men can have woman and their own family. It is better also for stability of society, since there are less frustrated men.
  1. I wonder how you could have thought the way you thought if you were raised in conservative Catholic family. I have atheist background (Central-Eastern Europe) and I have always considered mutual monogamy as natural and the right model of family, while infidelity was as a bad thing (I am not Christian, so sex outside marriage is normal, as well as serial monogamy or casual sex or FWB). I have never had real desire to have multiple girlfriends at the same time or even multiple families, I found it absurd, unthinkable, not right and inconvenient. Idea of onesided monogamy is unfair to me. Since I am a rules based guy, not a wild bad boy, when I found for the first time my male friends were unfaithful to their girlfriends, I felt like „how could he possibly do that?“ and not „wow, he is a cool guy for getting laid with another woman“. Now I am more in peace with reality but still it would be uncomfortable for me to do it since it goes against my core values.
  1. One point to one previous article. You correctly wrote that nice guys are guardians of social norms and that social norms cannot exist without people defending them. That actually implies that bad boys need and are kind of dependent on existence of nice guys. While they sometimes mock them and are arrogant to them as to people not knowing how to have fun and not being manly enough, they are exciting to women in contrast to them and their rules breaking is exciting only when other people follow the rules. When all nice guys start to behave like bad boys, this contrast disappears and social norms change or cease to be valid, so breaking them has no more effect.
  1. In the past I wrote you about my dilemma in relation to this Indonesian girl in long-term relationship (here: https://www.girlschase.com/content/how-screen-wife-and-mother). For your information, while she is still as lovable as she used to be, recently she got married with the same guy she was dating when I met her. So even your advice could not have worked in this case. Sometimes it is hopeless since beginning.


Thanks for your reply.


Lawliet's picture

Chase, you've been with me for half a decade or more. Despite not meeting, we've known each other for awhile. If you do fade away and call in quits with being the bachelor, don't be a stranger and hit me up by my email and let's stay in touch. It's like having a close friend who travelled to another country and never comes back. That feeling sucks.

TL01's picture

Thank you for this, Chase. Thank you.

Anonymous 's picture

Hey Chase, I just read a comment about you having a friend with a 400+ lay count. What did he work on and how did he improve himself to that point to get there?

I read one of them was charm. How do you get more of that?


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