Biggest age differences in dating you know of?

Jim Rome said:
I know this is off topic but the week I turned 25I had sex with 4 women one born in the 1960's, 1970's, 1980's and 1990's. My buddy is currently 30 dating a 21 year old and everyone makes fun of him for it.
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They're jelly. Always date the young (legal) ones until you cant anymore.
 
My grandfather is in his 70s, my step grandmother is in her late 30s..... we got a good laugh out of that when it happened. My aunt is 22 years younger than me.
 
When I was 21, I dated a 30 yr old...she was in a big panic to get married, so that was not much fun, haha...my wife now is 10yrs younger than me.
 
Last year I had a 3 month deal with a 20 year old (I'm 30). Like many others have posted, a ton of fun but damn was she annoying. 0 things in common besides having a good time. She was always trying to talk about her take on life and basically everything she said sounded like she heard it on MTV. Finally called it quits with her once she got too clingy and the fun didn't outweigh the hassle.
 
I'm pretty sure one of my cooks that is 46 is banging one of my 18 year old servers. Play on brother I'm not stopping you.
 
I'm 41 and my girlfriend is 26. We have a good relationship. The age thing isn't really an issue because her siblings are all much older than her so she gets my generation a bit.
 
jmac98 said:
Her and her 3 eggs.
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You have no idea. EVERYTHING was test, "How do you feel about [this]?" "What would you do in [this] situation?"

All kinds of ridiculous garbage...after a couple of months I dropped that crap.
 
I know a young lady who is college aged who is flirting about with some half-assed second rate member of nobility from Hungary or Albania or some other godforsaken place who keeps poncing about like some fruity medieval queen and is always sleeping until late afternoon claiming that he is feeling 500 years old and for once can his man servant have a damn bloody rare steak ready when he wakes up, and when it comes to Turkish immigrants it's bitch, bitch, bitch.
 
I knew a security guard at a casino who was close to 40 and going out with a 15 year old girl who worked at the bowling center in the same casino. The girl's dad was the guy's boss and he allowed the relationship to happen. This was awhile ago and last I heard from them, they got married and still together. I don't know too much details other than that.
 
From personal experience I found 20 to be divisible by 40.
But alas, I am married now and that is story of legend.
 
A buddy of mine in high school started screwing this older woman, who was the mother of a another friend of ours, when he was about 15 or 16. I'm not positive how old she was at the time but late 30's anyway. They were together for like 15 years.

Its weird how easy we all adjusted to our buddy nailing one of our other buddies mom.
 
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