Aging playboy needs some guidance

Knight of Roses

Senior Don Juan
Joined
Apr 17, 2018
Messages
298
Reaction score
276
Age
38
I'm not suppose to feel old, I mean 38 is not old right? But I celebrate my 38th tomorrow. And Idk, life feels a little different now. Work is good, expanding on some business projects to keep me entertained.

Personal life is getting kinda boring though. As many of you know, I have spent the last 5+ years frequenting bars/strip clubs and primarily dating 19-23 year old bartenders / waitresses / strippers. Yeah its been fun, but now its starting to get a bit boring.

On top of that, I feel isolated. Most of my close friends from years ago are all married off with kids and I hardly see them. Its been difficult to create / forge new friendships at this age.

I know several of you are older than me and still spinning plates. Tell me, what is your guys' day to day schedule like? How often do yall go out? Are you still chasing same type of women or have you changed? Made new friends or just accepted new solo hobbies?
 

BaronOfHair

Master Don Juan
Joined
Feb 14, 2024
Messages
2,443
Reaction score
1,019
Age
35
But I celebrate my 38th tomorrow. And Idk, life feels a little different now... Personal life is getting kinda boring though. As many of you know, I have spent the last 5+ years frequenting bars/strip clubs and primarily dating 19-23 year old bartenders / waitresses / strippers
38 is not 28, and the vapidness of girls in their late teens-early 20s is tough to ignore now... Next, we'll be discovering that if one lives among The Asmat of Papua New Guinea for long enough, he'll be talked into participating in a head hunt, and enjoying a meal of human flesh at least once or twice :eek: o_O

Happy BDay, BTW
 

TheGambino

Master Don Juan
Joined
Jun 25, 2013
Messages
2,704
Reaction score
930
Location
Somewhere
I invested the last 5 years in building my business and now I have a steady working team so I have way more freedom. My only focus and mission is working on myself. I’m on the road to a shredded body, and more money so I can wear even better, go on trips to nice places. I invested also heavily in friends and got a good social circle that likes the same things as I do. I just roam the bars every weekend where I met all of my friends. I moved to this new town 6 years ago where my life completely changed into this lifestyle. Now I’m focused on becoming even a better person, if your confident in your own skin you will attract better quality men and women that will attract even better looking women. People notice success and want to lift on it. Focus on yourself, become the best version of you and the rest will fall in place.
Good job.

I meet my women in bars (most are low quality) best women I met were randomly in supermarket, car wash, malls etc etc
 

holidayad_

Senior Don Juan
Joined
Dec 29, 2022
Messages
234
Reaction score
214
Age
25
I'm not suppose to feel old, I mean 38 is not old right? But I celebrate my 38th tomorrow. And Idk, life feels a little different now. Work is good, expanding on some business projects to keep me entertained.

Personal life is getting kinda boring though. As many of you know, I have spent the last 5+ years frequenting bars/strip clubs and primarily dating 19-23 year old bartenders / waitresses / strippers. Yeah its been fun, but now its starting to get a bit boring.

On top of that, I feel isolated. Most of my close friends from years ago are all married off with kids and I hardly see them. Its been difficult to create / forge new friendships at this age.

I know several of you are older than me and still spinning plates. Tell me, what is your guys' day to day schedule like? How often do yall go out? Are you still chasing same type of women or have you changed? Made new friends or just accepted new solo hobbies?
Don't know how to help you here, but I think it's a pretty good thread.

Hope you receive the advice you want.

Happy birthday.
 

BaronOfHair

Master Don Juan
Joined
Feb 14, 2024
Messages
2,443
Reaction score
1,019
Age
35
isn't that what ballgags are for?

View attachment 12736
If one is exceptionally motivated, he also has the option of heating up that Yakutian blade he purchased while visiting the Kobyaysky District on the stove, then relieving the irksome young maiden in his clothes of her tongue altogether :eek: :oops: Having to fiddle with ball gags quickly becomes exasperating
 

Don Jax

Don Juan
Joined
Jun 12, 2024
Messages
18
Reaction score
14
I'm not suppose to feel old, I mean 38 is not old right? But I celebrate my 38th tomorrow. And Idk, life feels a little different now. Work is good, expanding on some business projects to keep me entertained.

Personal life is getting kinda boring though. As many of you know, I have spent the last 5+ years frequenting bars/strip clubs and primarily dating 19-23 year old bartenders / waitresses / strippers. Yeah its been fun, but now its starting to get a bit boring.

On top of that, I feel isolated. Most of my close friends from years ago are all married off with kids and I hardly see them. Its been difficult to create / forge new friendships at this age.

I know several of you are older than me and still spinning plates. Tell me, what is your guys' day to day schedule like? How often do yall go out? Are you still chasing same type of women or have you changed? Made new friends or just accepted new solo hobbies?
OP,

For me, the key has been mixing things up and not getting too attached to one scene. I still enjoy hitting up the bars and clubs, but we all know that high-quality women are rare nowadays. And I'm pretty sure my chances of finding them in a club are pretty low.

That's why I try to keep myself busy in different ways. Traveling, writing, strolling around the city at night, and even going to a nice restaurant on a weekday. It helps me kill any bad feelings that might be poisoning my mind at that specific moment.

As for friends, it's true that many of them are settled down. I try to maintain the connection with them by doing activities that don't compromise their routine. Going to pubs, watching some games, and that sort of thing. I think it helps them clear their minds of the things that are bothering them in their marriages or relationships.

Find a good woman to settle down is something that crosses my mind sometimes. Maybe it would help with a few things. But after seeing so much out there, I know how difficult it is.

Generally speaking, the feeling of isolation (or living life as a lone wolf) is something we naturally get used to and learn to live with.

The positive thing is that we learn to live for ourselves and to satisfy ourselves.

Enjoy your birthday.
 

Rainman4707

Master Don Juan
Joined
Dec 30, 2012
Messages
1,614
Reaction score
534
I'm not suppose to feel old, I mean 38 is not old right? But I celebrate my 38th tomorrow. And Idk, life feels a little different now. Work is good, expanding on some business projects to keep me entertained.

Personal life is getting kinda boring though. As many of you know, I have spent the last 5+ years frequenting bars/strip clubs and primarily dating 19-23 year old bartenders / waitresses / strippers. Yeah its been fun, but now its starting to get a bit boring.

On top of that, I feel isolated. Most of my close friends from years ago are all married off with kids and I hardly see them. Its been difficult to create / forge new friendships at this age.

I know several of you are older than me and still spinning plates. Tell me, what is your guys' day to day schedule like? How often do yall go out? Are you still chasing same type of women or have you changed? Made new friends or just accepted new solo hobbies?
Sounds like you have no purpose.

I'm the same age as you, I have learnt that life is a tragedy, so i don't look to far up.

I know who i am. Physical activity is important to me. I'm curious and enjoy reading.

I enjoy travelling, learning about different parts of the world. I have just been up close with a tiger in Rathambore National park. , that made me feel alive.
 

BaronOfHair

Master Don Juan
Joined
Feb 14, 2024
Messages
2,443
Reaction score
1,019
Age
35
I have learnt that life is a tragedy...
With time, much of the events we once deemed tragedies become side-splitting farces. When I was in the second grade, the neighborhood MS-13 chapter told me and my entire family as much right before they sliced my older sister's skirt and panties off, then initiated her into womanhood via the aid of a lead pipe, all while forcing us to watch this entire spectacle

After the initial shock wore off, I was eventually able to chuckle over those bone heads having been so obtuse as to believe sis was still a virgin, by the time they'd gotten ahold of her o_O :confused:
 

BaronOfHair

Master Don Juan
Joined
Feb 14, 2024
Messages
2,443
Reaction score
1,019
Age
35
It helps me kill any bad feelings that might be poisoning my mind at that specific moment

I cannot encourage you vigorously enough to not simply listen, but to also apply everything offered in the above. Your thinking sounds extremely depressive
 

Bingo-Player

Master Don Juan
Joined
Jan 10, 2014
Messages
3,365
Reaction score
3,847
Location
uk
I'm 32 and am starting to recognise certain things I used to relish are wearing thin

The sort of hyper competitiveness of dating being one of them , In my 20's I used to genuinely believe I was the best any woman would ever get and this shone through in most interactions with them and usually ended up attracting them

but then I got in a 4 year LTR which broke down I turned 30 and everything started feeling a bit weird

i defenitley lost some of that edge,I've stopped dressing as immaculately / stylishly as I once did , my hairline is struggling , my enthusiasm and motivation for the gym is waining

I identified the problems and rapidly put a 5 year year plan in to try and achieve multiple milestones

I'm now 2 years into that so far i've built a few businesses , become self employed , relocated to the other side of the world and also began travelling Asia when I can

In the next 2 I hope to get a hair transplant , put more focus into health and nutrition redefine my style and hopefully find that woman I am going to settle with and who is going to have my children but totally aware time Is ticking

Each to his own but for me the playboy years were always going to need to be wrapped up by mid 30's

Unless you have serious and I mean serious wealth / social status dating / spinning is just too monotonous and time consuming after 30
 

Chow Mein

Senior Don Juan
Joined
Jun 9, 2024
Messages
231
Reaction score
155
@Knight of Roses
Do you attempt to keep in contact with your close friends that now have families? If not, I suggest doing so. These guys need support away from them as yourself in solitude. Try to give them a call twice and month just to catch up.

We’re around the same age and for the first time have endorsed the single lifestyle. I don’t think I will get tired of chasing women. Some occasions, I feel I’m missing out on building a future with someone by not being monogamous. It’s does bring out my emotional side, but logically, I’m building that relationship with the other person on a different level. There are those that stick around because they fear losing you forever. They know I will not commit to them or anyone else and it is accepted.

I'm 32 and am starting to recognise certain things I used to relish are wearing thin

The sort of hyper competitiveness of dating being one of them , In my 20's I used to genuinely believe I was the best any woman would ever get and this shone through in most interactions with them and usually ended up attracting them

but then I got in a 4 year LTR which broke down I turned 30 and everything started feeling a bit weird

i defenitley lost some of that edge,I've stopped dressing as immaculately / stylishly as I once did , my hairline is struggling , my enthusiasm and motivation for the gym is waining

I identified the problems and rapidly put a 5 year year plan in to try and achieve multiple milestones

I'm now 2 years into that so far i've built a few businesses , become self employed , relocated to the other side of the world and also began travelling Asia when I can

In the next 2 I hope to get a hair transplant , put more focus into health and nutrition redefine my style and hopefully find that woman I am going to settle with and who is going to have my children but totally aware time Is ticking

Each to his own but for me the playboy years were always going to need to be wrapped up by mid 30's

Unless you have serious and I mean serious wealth / social status dating / spinning is just too monotonous and time consuming after 30
Your 30’s will be a blast for you if your life is in order, as you’re doing. I found that in order to know what you will settle for, you need to date as many women as possible to figure it out.
 

BaronOfHair

Master Don Juan
Joined
Feb 14, 2024
Messages
2,443
Reaction score
1,019
Age
35
I can't help but be reminded of the opening line of TC Boyle's short story "The Little Chill", when reading this thread:

"Hal had known Rob and Irene, Jill, Harvey, Tottle, and Pesky since elementary school, and they were all 40 going on 60."

Only difference here... We've got a few 30somethings who speak as if they're in their 90s
 

Dr.Suave

Moderator
Joined
Mar 6, 2017
Messages
3,812
Reaction score
4,137
I'm not suppose to feel old, I mean 38 is not old right? But I celebrate my 38th tomorrow.
Sounds like the mid-life crisis arrived a couple of years early. You are not old, you are younger than Chris Hemsworth. Tom brady was like 43 when he was still winning super bowls. Happy birthday bro

On top of that, I feel isolated. Most of my close friends from years ago are all married off with kids and I hardly see them. Its been difficult to create / forge new friendships at this age.
Friends grow apart, for a number of reasons. Have you considered getting closer to family? Cousins, uncles, etc

Personal life is getting kinda boring though. As many of you know, I have spent the last 5+ years frequenting bars/strip clubs and primarily dating 19-23 year old bartenders / waitresses / strippers. Yeah its been fun, but now its starting to get a bit boring.
You are tired of spinning plates that are not worthy of LTR. I think you could use some hobbies that have nothing to do with women, hobbies you actually enjoy. You could end up attracting girls that like the same hobbies or girls who just like to be around someone who is authentically enjoying said hobbies. I think @The Duke has some insights of this.
 

Solomon

Master Don Juan
Joined
Sep 28, 2008
Messages
5,542
Reaction score
2,701
Location
Inside her mind
I'm 32 and am starting to recognise certain things I used to relish are wearing thin

The sort of hyper competitiveness of dating being one of them , In my 20's I used to genuinely believe I was the best any woman would ever get and this shone through in most interactions with them and usually ended up attracting them

but then I got in a 4 year LTR which broke down I turned 30 and everything started feeling a bit weird

i defenitley lost some of that edge,I've stopped dressing as immaculately / stylishly as I once did , my hairline is struggling , my enthusiasm and motivation for the gym is waining

I identified the problems and rapidly put a 5 year year plan in to try and achieve multiple milestones

I'm now 2 years into that so far i've built a few businesses , become self employed , relocated to the other side of the world and also began travelling Asia when I can

In the next 2 I hope to get a hair transplant , put more focus into health and nutrition redefine my style and hopefully find that woman I am going to settle with and who is going to have my children but totally aware time Is ticking

Each to his own but for me the playboy years were always going to need to be wrapped up by mid 30's

Unless you have serious and I mean serious wealth / social status dating / spinning is just too monotonous and time consuming after 30
Props to you for following through with your 5 year plan, you should do an updated thread on that love to see it, this is the type of shyt that motivates me. As soon as I read it I realized I had stuff written down 3 years ago and I'm lagging behind

I will say this as a guy who is 40 spinning plates becomes time-consuming especially if you are on the road to success or self-improvement. From Jan-May I went on 4-5 dates, a couple of girls I saw again most I didn't. The first two weeks of June I have gone on 7 dates I could have gone on more but honestly, I realized 1. The women weren't worth the hassle i.e. high maintenance or logistics 2. Even the 7 dates I went on were time consuming and it adds up even if you are doing cheap dates

I'm content with one chick who can I see 3X times a week but that's me
 

LucianoM

Senior Don Juan
Joined
Jul 21, 2020
Messages
331
Reaction score
495
Location
California
I'm not suppose to feel old, I mean 38 is not old right? But I celebrate my 38th tomorrow. And Idk, life feels a little different now. Work is good, expanding on some business projects to keep me entertained.

Personal life is getting kinda boring though. As many of you know, I have spent the last 5+ years frequenting bars/strip clubs and primarily dating 19-23 year old bartenders / waitresses / strippers. Yeah its been fun, but now its starting to get a bit boring.

On top of that, I feel isolated. Most of my close friends from years ago are all married off with kids and I hardly see them. Its been difficult to create / forge new friendships at this age.

I know several of you are older than me and still spinning plates. Tell me, what is your guys' day to day schedule like? How often do yall go out? Are you still chasing same type of women or have you changed? Made new friends or just accepted new solo hobbies?
You have no direction or purpose and your hapiness depends on external factors(girls). Its hard to breakout of that whirlpool once you're in it and honestly I don't know what else there is. Hobbies are bull****. Genuine male friends are a good option though but just as hard to find as a good girl these days.
 

Travel memoir21

Master Don Juan
Joined
Feb 20, 2020
Messages
651
Reaction score
503
Age
38
Location
Rio Grande Valley, Texas
You have no direction or purpose and your hapiness depends on external factors(girls). Its hard to breakout of that whirlpool once you're in it and honestly I don't know what else there is. Hobbies are bull****. Genuine male friends are a good option though but just as hard to find as a good girl these days.
You probably have a rotten spiritual life as well.

Simple things such as prayer, reading the scriptures, having thanksgiving/ gratitude sessions with friends and love ones and giving back to the poor would probably do you some good.

You sound way too self absorbed bro.
 

LucianoM

Senior Don Juan
Joined
Jul 21, 2020
Messages
331
Reaction score
495
Location
California
You probably have a rotten spiritual life as well.

Simple things such as prayer, reading the scriptures, having thanksgiving/ gratitude sessions with friends and love ones and giving back to the poor would probably do you some good.

You sound way too self absorbed bro.
I think youre right, but thats just a side effect of being a life long bachelor. How am I supposed to care for others when I've been a lone wolf all my life?
 

Travel memoir21

Master Don Juan
Joined
Feb 20, 2020
Messages
651
Reaction score
503
Age
38
Location
Rio Grande Valley, Texas
I think youre right, but thats just a side effect of being a life long bachelor. How am I supposed to care for others when I've been a lone wolf all my life?
I think there's a few older and more enlightened dudes out here who can answer that question far better than me.

But personally I recommend Volunteering for something whether it's a homeless shelter, foodbank or a children's hospital. Then you need a sense of community which is why I recommend going to a Church.

And when I mean Church, not your feminize, sissy boy, liberal pandering churches. But with a Strong, righteous masculine Pastor who knows what he's talking about.
 
Top