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Largest age difference you've had in dating or hookup...

J

JLORYFSU!

Freshman
Apr 6, 2002
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What is the largest difference in years you've had when it comes to dating someone or doing the nasty? Don't include Costa Rican hookers or any other escorts, lady of the evening.

Largest I've had in a relationship was earlier this yr. It was a 12 yr difference. I'm 49, she is 37.

Largest I've had in a casual hookup was this week. She is 23 and originally from Brazil. Not going to turn into anything but definitely was fun.

Any Hugh Hefners in the Locker Room?
 
I typically dated older women. When I was 19, I dated someone who was 24...at 22 I briefly dated someone 33. My wife is 4.5 years older than me.

Now that I'm older (and married), I get interest from younger women. Go figure.
 
Jeeze what a way to humble-brag. I can't believe that no one has asked for pics yet!

When I was in the Army I would go home and visit my Dad. His wife's best friend was a recently divorced smoke show. Super hot. She was 37 or 38. I was about 20. She used me for my fitness level and stamina.

I actually kept a couple of pictures of her for instances just like this but they are in my home computer. I'm traveling for business. I'll toss them up here later.

This went on for a couple of years. I hit it until I was 22/23 anytime I went home and wasn't in a rationship.

All my buddies called her grandma.
 
FreeFlyNole said:
Jeeze what a way to humble-brag. I can't believe that no one has asked for pics yet!

When I was in the Army I would go home and visit my Dad. His wife's best friend was a recently divorced smoke show. Super hot. She was 37 or 38. I was about 20. She used me for my fitness level and stamina.

I actually kept a couple of pictures of her for instances just like this but they are in my home computer. I'm traveling for business. I'll toss them up here later.

This went on for a couple of years. I hit it until I was 22/23 anytime I went home and wasn't in a rationship.

All my buddies called her grandma.
Click to expand...

I'm making a note of this for reminder purposes.


And the OP definitely needs to post pics to document this event.
 
I think around a 4-5 year age difference. A few hook ups where I was post college but before meeting the wife.
 
Last year I did the dirty with a 41 year old then a 42 year old. Currently working on a 62.

I'm 25.
 
YoungNole said:
Last year I did the dirty with a 41 year old then a 42 year old. Currently working on a 62.

I'm 25.
Click to expand...

I had a 30 something year old part time girlfriend the year I graduated high school. I dated another 30 something year old not long after that. Her baby daddy was Artimus Pyle from Lynerd Skynerd, met him a few times. Every other girl was within a few years of my age.
 
My ex-fiance was 4 years younger than me. That's the biggest gap for me. Right now I'm 31, newly single, and there are several cute girls in my office that must be in their early 20's. I keep second guessing whether or not I'd be a creep if I tried talking to any of them. I guess I shouldn't worry about age and just go by how mature they act.
 
jamnolfin said:
I had a 30 something year old part time girlfriend the year I graduated high school. I dated another 30 something year old not long after that. Her baby daddy was Artimus Pyle from Lynerd Skynerd, met him a few times. Every other girl was within a few years of my age.
Click to expand...

No drama, no insecurities (other than the occasional reassurance they still look good), no false ideations about commitments. Older women do it better.
 
When I was 39 I was hooking up with a 19 year old receptionist. I never took her out but she would come over and pregame at my house for drinks and banging.
 
I was 16 and she was the wife of the golf pro(30ish) were I lived near Daytona.
 
When I was around 32ish or so I was kind of dating this 21 year old. Man oh man was she hot, dear lord if I could go back for a night. When I was mid to early 20's I hooked up with a few mid to late 30 year olds, maybe a few were 40. All good looking and happily divorced just looking for one night stands...even though I hooked up with many of them on multiple occasions. There were never any dates though. Met them for first time at a bar while out, hooked up, kept their numbers and did booty calls from there on out....easy peasy, good lays too.

The 21 year old was the babysat my nieces and nephews. She watched them since she was 15, had known her forever. One night we all came back to my sisters house where she was babysitting, I was liquored up and going back out. She asked where I was going and if she could come...it was on like donky kong.
 
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TarponSpringsNole said:
25 yrs. I was 43, she was 18. Damn. That age difference looks gross when it's written down.
Click to expand...

Really? When I was right out of college I was about 23-24 I spurned the advances of a friend of a friend who was in her 40's and I regret it looking back. I bet that would have been an educational experience well worth the time. She could certainly move on the dance floor.
 
BelemNole said:
Really? When I was right out of college I was about 23-24 I spurned the advances of a friend of a friend who was in her 40's and I regret it looking back. I bet that would have been an educational experience well worth the time. She could certainly move on the dance floor.
Click to expand...

Yes. Really. She was a naive and innocent thing. Guess I ruined that.
 
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Dang, I left out my biggest age difference.....I slept with my high school prom queen's mom when I was in College. I was a senior, 22 years old and her mom, Betty, was probably early to mid 50's....It was a New Year's Day and I was home from college watching Miami vs Penn st for the National Title (Vinny camo Canes were upset) and I met Betty at the bar.....I was hammered and we sucked face in the bar,,,,when I left with her, the bar patrons were yelling "Take it easy on him, Betty, he is just a kid".....one of the worst lays of my life and she was hammered and kept saying "Do u love Betty, Betty loves you".....shuddering thinking about it!
 
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From two sides of the spectrum:

When I was 31 I was involved with a stunning 50ish year old European woman who would bring her real estate clients to an ocean front condo project I helped develop. Not only was she beautiful & athletic, she was a very savvy business woman and sold multiple units in this project. She was a major catalyst in its success. While our physical relationship ended long ago, she remains a close friend of mine.

At age 46 and only for a few months, I dated a 22 year old Czech girl who had recently moved to Florida. She was ending a relationship with an abusive boyfriend that played drums in a house band in a night club that my friend owned. We always seemed to be sitting at the corner of the bar chatting and one night she just went home with me. Never for a moment did I expect the relationship to last beyond a couple encounters, but we had a bit of chemistry and had plenty of fun together. I felt blessed every time we jumped in bed and I made certain I savored every moment. My buddies still give me props every time we go to breakfast at the bakery she and her husband now own.
 
My wife is 10 years younger than me and that's the biggest age difference I've ever had. Always dated younger, but 10 is the biggest gap.
 
I was 25, she was 48. We hooked up in her car.

We couldn't go back to her place, because her son was home from college and had friends over.
 
Currently, i'm 33 she is 20. The biggest age gap i've had was 14 years, me being 33 she (not the same one) being 19, who is the sister of another one i've had (me 32, she 23)...all in the past year! It's been wild!
 
At 16 hooked up with the 22 year old boarder at my buddy's grandmothers house. Only 6 years but as a function of percentage it's by far my largest.
 
I was 17 she was 32. When I was that age the hottest women on the planet IMO were the well taken care 30-37 yr olds. Today I am 57 and I still think the well taken care of 30-37 yr olds are the hottest women on the planet. Difference is now they have no interest in someone who could be their child's papa.
 
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