u/Dramatic_Channel52

Is anyone else just bored with the doldrums of life? Is this a midlife crisis? Dipping my toes here to see if someone else is in the same situation and interested in adding some excitement to my life. I’m very new to this, so really not interested in others that have done this before. I’d prefer we have experiences together than anything else.

About me:
50 yo man
- married with kids
- Silver Fox
- well educated with a white collar career
- people would describe me as a social butterfly and someone who can command a room.

What I’m looking for:
- preferably 43+
- well educated, white-collar professional only (must be in same socioeconomic status as me)
- must be in good shape
- must work in city
- bonus if you can make me laugh

Looking to build a mental connection first. Feel free to drop me a DM and see if we connect. At worst, we can entertain each other over the long weekend!

How old were you when you learned this was sung by the Pointer Sisters! (Yes, that Pointer Sisters!)

If you heard the song and remember the pinball running through the machine, keep reading fellow GenXer!

I want to wax nostalgia about the growing up during the 80s and 90s. A childhood that didn’t involve social media, parental tracking, and lots of outdoor time. Oh, what I would do to spend another warm summer night in July with not a worry in the world.

Today I’m a young 50 year old soul, married, and living my life telling my kids about growing up in a different time. I enjoy traveling, both to new and old locations.

I’m seeking banter through my day and evening. I have an otherwise healthy relationship at home and prefer to keep it that way. I am NOT interested in spouse bashing. Ideally, you’re married with some kids, professional, and loves being a parent.

I connect best with those closer to my age for both nostalgia and guidance.

If you made it this far, what was your favorite Trapper Keeper in the fourth grade and why was it a Lisa Frank?

🎶 Electric word, life
It means forever, and that's a mighty long time
But I'm here to tell you there's something else:
The afterworld

A world of never ending happiness
You can always see the sun, day or night 🎸

If you read all of that in a particular voices, you have great taste in music and who I want to connect with!

I’m solidly GenX looking to wax nostalgia about the greatest childhood ever.

Today, I'm 49 and fully embrace all things GenX. As a point of mention as well, I'm not white, just to get that out of the way, though I grew up mostly with white. I’d like to connect with someone that is married, isn’t afraid to catch feelings, and is open for occasional and spontaneous lunch and coffee dates through the week. Happy Hours and the such aren’t out of the question either. My OPSEC is tight and I have the financial means to run this relationship and I’d expect you to as well.

I’m looking for somebody that identifies primarily as GenX, Xennial, or maybe an older Millennial with some kids that keep you busy. I think I get along best with those that have an otherwise healthy relationship with their spouse, but feel like the physical aspect is missing for one reason or another.

If any of this resonates with you, let’s chat. Let’s talk about the greatest childhood. One that didn’t involve social media, smart phones, our parents knowing where we were at every minute, and enjoying a carefree life of no worries.

If you made it this far, tell me, what other excellent musicians do you enjoy?

🎶 Electric word, life
It means forever, and that's a mighty long time
But I'm here to tell you there's something else:
The afterworld

A world of never ending happiness
You can always see the sun, day or night 🎸

If you read all of that in a particular voices, you have great taste in music and who I want to connect with!

I’m solidly GenX looking to wax nostalgia about the greatest childhood ever.

Today, I'm 49 and fully embrace all things GenX. As a point of mention as well, I'm not white, just to get that out of the way, though I grew up mostly with white. I’d like to connect with someone that is married, isn’t afraid to catch feelings, and is open for occasional and spontaneous lunch and coffee dates through the week. Happy Hours and the such aren’t out of the question either. My OPSEC is tight and I have the financial means to run this relationship and I’d expect you to as well.

I’m looking for somebody that identifies primarily as GenX, Xennial, or maybe an older Millennial with some kids that keep you busy. I think I get along best with those that have an otherwise healthy relationship with their spouse, but feel like the physical aspect is missing for one reason or another.

If any of this resonates with you, let’s chat. Let’s talk about the greatest childhood. One that didn’t involve social media, smart phones, our parents knowing where we were at every minute, and enjoying a carefree life of no worries.

If you made it this far, tell me, what other excellent musicians do you enjoy?

Q: Why should I consider an older model?
A: Proven reliability, steel and chrome: no flimsy plastic parts. Guaranteed no AI. They don’t make ‘em like they used to.

Q: What makes you so special?
A: Debatably charming, not a creep, and despises ghosting. On Reddit, isn’t that special?

Q: Are you even the least bit good looking and fit?
A: This is a pointless question. Are you going to believe what any man says about his own looks? But turns out I’m gorgeous. Pictures available, guaranteed to be from the current decade.

Q: Are you good in bed?
A: See the last answer, but even more so. Look, there’s a free trial offer. What more do you need? I am… unselfish.

Q: Do you accept credit cards?
A: Yes, American Express Gold and Platinum only. The 3% fee could be waived.

Q: What have previous customers said about you?
A: “Solid value, works as advertised, has all his teeth.” “Better looking than my sister’s husband” “Took off a star because mine came in a damaged box” “OMG, that tongue.” “I changed my name and came back for a free drive 11 times. He never noticed.”

Q: Do you send dick pics?
A: No, but thanks for asking!

Q: Are you married? kids? Done this before?
A: Yes, yes, yes.

Q: What traits are you looking for in a partner?
A: Honesty, sense of humor, and energy that matches mine. Inexplicable, magical magnetism never hurts.

Q: What else should I know?
A: I’m a kind, open minded man, relatively normal, I’m very honest and you’ll like me.

Please note: free beverage for the 1st customer

Q: Why should I consider an older model?
A: Proven reliability, steel and chrome: no flimsy plastic parts. Guaranteed no AI. They don’t make ‘em like they used to.

Q: What makes you so special?
A: Debatably charming, not a creep, and despises ghosting. On Reddit, isn’t that special?

Q: Are you even the least bit good looking and fit?
A: This is a pointless question. Are you going to believe what any man says about his own looks? But turns out I’m gorgeous. Pictures available, guaranteed to be from the current decade.

Q: Are you good in bed?
A: See the last answer, but even more so. Look, there’s a free trial offer. What more do you need? I am… unselfish.

Q: Do you accept credit cards?
A: Yes, American Express Gold and Platinum only. The 3% fee could be waived.

Q: What have previous customers said about you?
A: “Solid value, works as advertised, has all his teeth.” “Better looking than my sister’s husband” “Took off a star because mine came in a damaged box” “OMG, that tongue.” “I changed my name and came back for a free drive 11 times. He never noticed.”

Q: Do you send dick pics?
A: No, but thanks for asking!

Q: Are you married? kids? Done this before?
A: Yes, yes, yes.

Q: What traits are you looking for in a partner?
A: Honesty, sense of humor, and energy that matches mine. Inexplicable, magical magnetism never hurts.

Q: What else should I know?
A: I’m a kind, open minded man, relatively normal, I’m very honest and you’ll like me.

Please note: free beverage for the 1st customer

If you’re of a certain age, you remember MTV VJs. We even watched MTV News.

Crazy to think how much influence that one channel had on an entire generation.

In fact, I just learned that Kurt Loder is now 81 years old (eighty-one!!) … whattttttt?!? MTV is where I leaned about Kurt Cobain’s death. Tabitha Soren for sure was my favorite, but Kurt Loder seemed like a cool dude that I’d love to hang out with.

Ah, me. I’m 50, married, kids, the gambit. I love sports (MLB and NFL are my jam), traveling, and spending time catching up with friends over beers/cocktails.

I’m looking for someone that matches my energy. Someone who loves talking about our great 80s and 90s childhood and kind of scratches their heads at the weird shit our kids do today.

If any of this sounds like you - drop me a line. Tell me who was your favorite MTV VJ?

Entering the very end of my 40s (yikes) and been jonesin’ for some solid falafels of late. I work in the loop, pretty close to Wabash where I would say some of the best falafels are in Chicago.

Anybody down to meet for some falafels for lunch?

Full disclosure- I’m married, would prefer you are as well. I work in the loop, live well outside of it and am not beneath a little flirting with the right person too 😉

Let’s chat!

Entering the very end of my 40s (yikes) and been jonesin’ for some solid falafels of late. I work in the loop, pretty close to Wabash where I would say some of the best falafels are in Chicago.

Anybody down to meet for some falafels for lunch?

Full disclosure- I’m married, would prefer you are as well. I work in the loop, live well outside of it and am not beneath a little flirting with the right person too 😉

Let’s chat!

Because that's what I'm looking for. A married man looking to connect with a woman, married, or understanding, open-minded, interested.

"Affair" can sound wrong in many ways but when it's a friendship, it's certainly not wrong. And I'm not here to hide it forever. Respect and true feelings will often change lives.

There are many reasons why a husband or wife want to have an additional friendship. Our situations are all unique and it takes an open mind and non-judgemental stance to do this. Nothing is ever set in stone. People change their lives all the time and when they say they are not because they just want a secret affair, they still change their lives. I hope you understand what I am getting at.

I seek a friendship, a long-lasting relationship. I'm not looking to hide it away for the rest of my life and neither should you. But you do what you feel is best for you. Discretion is certainly key for me at first in order to find that true friend.

I'm college educated, fit, young at heart and in great shape. I'm definitely looking for a woman around the same age as me.

Please be also active, body-positive. I love a natural body and leaner body shape (curves are ok 🙂); preferably work white collar role.

For more on me, please visit my other posts, accessible from my profile. I'm a kind man, funny, often sarcastic, but always positive regarding my life and others' lives, definitely reject extremism.

Would love a reply from someone who's also looking to make their life happier, not more complicated. Even if we just end up talking, let's enrich our lives.

Because that's what I'm looking for. A married man looking to connect with a woman, married, or understanding, open-minded, interested.

"Affair" can sound wrong in many ways but when it's a friendship, it's certainly not wrong. And I'm not here to hide it forever. Respect and true feelings will often change lives.

There are many reasons why a husband or wife want to have an additional friendship. Our situations are all unique and it takes an open mind and non-judgemental stance to do this. Nothing is ever set in stone. People change their lives all the time and when they say they are not because they just want a secret affair, they still change their lives. I hope you understand what I am getting at.

I seek a friendship, a long-lasting relationship. I'm not looking to hide it away for the rest of my life and neither should you. But you do what you feel is best for you. Discretion is certainly key for me at first in order to find that true friend.

I'm college educated, fit, young at heart and in great shape. I'm definitely looking for a woman around the same age as me.

Please be also active, body-positive. I love a natural body and leaner body shape (curves are ok 🙂); preferably work white collar role.

For more on me, please visit my other posts, accessible from my profile. I'm a kind man, funny, often sarcastic, but always positive regarding my life and others' lives, definitely reject extremism.

Would love a reply from someone who's also looking to make their life happier, not more complicated. Even if we just end up talking, let's enrich our lives.

Huge Cubs fan and maybe a bigger fan of cunnilingus. Would love to go to a game and then treat my fellow Cubs fan to some delightful oral.

I’m 49 (with a birthday coming up soon, and yes, I can prove it) and in full disclosure I’m married. I’d prefer you’re married as well for reasons that don’t need to be stated.

Let chat here, move to get a vibe check over drinks, then hit a Cubs game. If you’re nice, maybe we can hit the 1914 seats … 🤔

Early 50s, married, white collar executive visiting Chicago week after next (well, May 18th) visiting clients and some teams based locally.

I have 2 evenings free - I’m also a big baseball fan, would love to visit Wrigley with the right person

Staying off North Michigan Ave in the Gold Coast

… and if you were *lucky*, the DJ didn’t talk over the intro. 😡

I do have Spotify today, but man, it was so much more fun to make mixtapes off the radio, wasn’t it?

Today, I’m late 40s and fully embrace all things from my 80s and 90s childhood. I’m a white-collar professional, married with 2 boys. I enjoy watching and attending live sports (baseball and football are my jam, with some college ball thrown in there), and working out. I also enjoy visiting breweries and places to meet friends to catch up and chat.

There is no better feeling than chatting with friends that you haven’t seen in a long time while enjoying a few beers. My beverages of choice depends on the time of day (and sometimes season of the year) - coffee, cocktails, and cold beers are generally good hits with me.

Ideally, I’d like to connect with someone that is married, with some kids. I’d love to chat with someone that is local to Chicago and might be open to potentially meeting if our stars align.

If any of this interests you, drop me a line and tell me a bit about yourself … and maybe what was on that mix tape!

… and if you were *lucky*, the DJ didn’t talk over the intro. 😡

I do have Spotify today, but man, it was so much more fun to make mixtapes off the radio, wasn’t it?

Today, I’m late 40s and fully embrace all things from my 80s and 90s childhood. I’m a white-collar professional, married with 2 boys. I enjoy watching and attending live sports (baseball and football are my jam, with some college ball thrown in there), and working out. I also enjoy visiting breweries and places to meet friends to catch up and chat.

There is no better feeling than chatting with friends that you haven’t seen in a long time while enjoying a few beers. My beverages of choice depends on the time of day (and sometimes season of the year) - coffee, cocktails, and cold beers are generally good hits with me.

Ideally, I’d like to connect with someone that is married, with some kids. I’d love to chat with someone that is local to Chicago and might be open to potentially meeting if our stars align.

If any of this interests you, drop me a line and tell me a bit about yourself … and maybe what was on that mix tape!

… and if you were *lucky*, the DJ didn’t talk over the intro. 😡

I do have Spotify today, but man, it was so much more fun to make mixtapes off the radio, wasn’t it?

Today, I’m late 40s and fully embrace all things from my 80s and 90s childhood. I’m a white-collar professional, married with 2 boys. I enjoy watching and attending live sports (baseball and football are my jam, with some college ball thrown in there), and working out. I also enjoy visiting breweries and places to meet friends to catch up and chat.

There is no better feeling than chatting with friends that you haven’t seen in a long time while enjoying a few beers. My beverages of choice depends on the time of day (and sometimes season of the year) - coffee, cocktails, and cold beers are generally good hits with me.

Ideally, I’d like to connect with someone that is married, with some kids. I’d love to chat with someone that is local to Chicago and might be open to potentially meeting if our stars align.

If any of this interests you, drop me a line and tell me a bit about yourself … and maybe what was on that mix tape!

How old were you when you learned this was sung by the Pointer Sisters! (Yes, that Pointer Sisters!)

If you heard the song and remember the pinball running through the machine, keep reading fellow GenXer!

I want to wax nostalgia about the growing up during the 80s and 90s. A childhood that didn’t involve social media, parental tracking, and lots of outdoor time. Oh, what I would do to spend another warm summer night in July with not a worry in the world.

Today I’m a young 50 year old soul, married, and living my life telling my kids about growing up in a different time.

I enjoy traveling, both to new and old locations. I’m seeking banter through my day and evening. I have an otherwise healthy relationship at home and prefer to keep it that way. I am NOT interested in spouse bashing.

Ideally, you’re married with some kids, professional, and loves being a parent. I connect best with those closer to my age for both nostalgia and guidance.

If you made it this far, what was your favorite Trapper Keeper in the fourth grade and why was it a Lisa Frank?

You really can’t deny it, can you?

If you …
* Spent your Friday evenings at Blockbuster Video looking for movies to rent
* Shopped at Sam Goody’s, Walden Books, Merry Go Round at the mall
* Lined up to buy a CD on Monday night for new release Tuesday
* Had a favorite Lisa Frank Trapper Keeper
* Covered your textbooks in paper bags
* Played four square on the playground
* Got your news from MTV with Kurt Loder and Tabitha Soren

… then you may have had the greatest childhood!

Today, I am a 50 year old married white collar male with kids. I live outside of Chicago and work in the Loop. I enjoy traveling, both to new and old locations. I’m looking for someone that works in or near the Loop, and is open to spontaneous (and planned) lunch or coffee dates and the occasional happy hours after work.

I enjoy chatting either over a coffee, beer, or cocktail. In my career, I’ve learned, personal relationships matter. I’m flirty and seek banter through my day and evening. I want to hear about your day.

My OPSEC is tight and would expect yours to be as well. I have the financial cover to run a relationship like this and would expect you to as well.

If you made it this far, what was your favorite Trapper Keeper in the fourth grade and why was it a Lisa Frank?

You really can’t deny it, can you?

If you …
* Spent your Friday evenings at Blockbuster Video looking for movies to rent
* Shopped at Sam Goody’s, Walden Books, Merry Go Round at the mall
* Lined up to buy a CD on Monday night for new release Tuesday
* Had a favorite Lisa Frank Trapper Keeper
* Covered your textbooks in paper bags
* Played four square on the playground
* Got your news from MTV with Kurt Loder and Tabitha Soren

… then you may have had the greatest childhood!

Today, I am a 50 year old married white collar male with kids. I live outside of Chicago and work in the Loop. I enjoy traveling, both to new and old locations. I’m looking for someone that works in or near the Loop, and is open to spontaneous (and planned) lunch or coffee dates and the occasional happy hours after work.

I enjoy chatting either over a coffee, beer, or cocktail. In my career, I’ve learned, personal relationships matter. I’m flirty and seek banter through my day and evening. I want to hear about your day.

My OPSEC is tight and would expect yours to be as well. I have the financial cover to run a relationship like this and would expect you to as well.

If you made it this far, what was your favorite Trapper Keeper in the fourth grade and why was it a Lisa Frank?

You really can’t deny it, can you?

If you …
* Spent your Friday evenings at Blockbuster Video looking for movies to rent
* Shopped at Sam Goody’s, Walden Books, Merry Go Round at the mall
* Lined up to buy a CD on Monday night for new release Tuesday
* Had a favorite Lisa Frank Trapper Keeper
* Covered your textbooks in paper bags
* Played four square on the playground
* Got your news from MTV with Kurt Loder and Tabitha Soren

… then you may have had the greatest childhood!

Today, I am a 50 year old married white collar male with kids. I live outside of Chicago and work in the Loop. I enjoy traveling, both to new and old locations. I’m looking for someone that works in or near the Loop, and is open to spontaneous (and planned) lunch or coffee dates and the occasional happy hours after work.

I enjoy chatting either over a coffee, beer, or cocktail. In my career, I’ve learned, personal relationships matter. I’m flirty and seek banter through my day and evening. I want to hear about your day.

My OPSEC is tight and would expect yours to be as well. I have the financial cover to run a relationship like this and would expect you to as well.

If you made it this far, what was your favorite Trapper Keeper in the fourth grade and why was it a Lisa Frank?