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

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I was 21 and she was 38. Went from a one nighter to lasting a few months. Ended up being the reliable booty call for about a year after we broke it off. When she'd travel for work I'd dog sit for her, drive her Bimmer to pick up chicks, then greet her when she got home. Ended when I met someone.
 
I was 19 and working as a lifeguard at the Don Cesar - A very successful summer, but the one that got away was this 28 year old who habitually wore hells with her swimsuit to the pool.....she kept suggesting we meet at this or that bar which, of course, I could not necessarily get into because I was underage.
 
was 19 and dated a 17 year old. It only SEEMED like a larger age difference.
 
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.

Well?
 
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.

Sounds pretty close to the standard rule of thumb: One half your age plus 7 years -- and anything above, is ok.

You sound like me when I was in my 30s and was concerned about dating in the 20s, especially around the office. In hindsight I say go for it.....
 
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?



4 years older and 25 years younger......

The 4 years older was like hammering a cactus.
 
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