Straight guy. Had a fairly intense romance with a 35-year-old when I was 24.
Didn’t work out, as I was still enjoying the freedom of independent adulthood, while she was feeling the pressure of advancing years and was getting desperate for a husband and a kid. The sex was good, though.
[QUOTE=Ensign Edison]
Or a hookup, perhaps.
Mine’s easy. When I was fourteen I had a romantic relationship with a twenty-seven-year-old. No nudity, but it definitely counts. Sometimes I become alarmed thinking that I’m still not even quite as old as he was when he was hounding me at half my age.
Oh, for the sake of the record, please state your gender and orientation if you are willing to do so. I’m curious if there are correlations.
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When I was 27 my girlfriend was 42, so that’s a fifteen year period.
When I was 30 I had a 40 year old girlfriend; she called me “Daddy,” which made things significantly weirder than the other.
[QUOTE=Skald the Rhymer]
When I was 27 my girlfriend was 42, so that’s a fifteen year period.
When I was 30 I had a 40 year old girlfriend; she called me “Daddy,” which made things significantly weirder than the other.
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By period, of course, I mean difference.
And I’m a straight male.
When I was 30, I dated a gal who was in her early-to-mid 50s for a while.
I can’t say exactly how old she was, because I don’t know; she told me she was 41 and I believed her. Not until she broke things off did she casually say, “And by the way, I’m a lot older than I told you before.”
My wife (the most wonderful woman in the world) is 15 1/5 years older than I am. We met here on the boards 5 1/2 years ago and we will be celebrating our 4th wedding anniversary next month 
I’m 32 (male), my girlfriend is 47. We’ve been together for almost a year.
I’m 36 (straight female) and my SO of three years is 26.
Four and a half years, so far, when I was 23 and she was 27.
24 year old bisexual male.
Female, straight.
One hookup where he was 5 years younger.
One guy who asked me out who was 23 years older (but what really squeeked me out was the way he treated his kid, even more than his gut).
Straight male of 26 and my girlfriend is 44 years old. We’ve been together for about a year and a half now and we have a 5 month old daughter.
Female, straight, eight years, he’s the younger, it didn’t work because he was too young.
Now I wouldn’t want to date a guy under the age of 25.
Heteroflexible male, 28. Biggest age difference: three years and change. Not too impressive, all things considered.
[QUOTE=Priceguy]
Heteroflexible male, 28. Biggest age difference: three years and change. Not too impressive, all things considered.
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That’s a great, elegant term. Mind if I borrow it?
37 gay male here. Always tended to go for men older than me. The first man I dated was 17 years older. Partner_Slip is 11 years my “better”.
As far as deep, meaningful, one-night relationships, I’ve hooked up with guys in their 50s when I was in my 20s.
Didn’t often “date” (in whatever sense I used the word at the time) men my age or younger.
[QUOTE=Freudian_Slip]
That’s a great, elegant term. Mind if I borrow it?
[/QUOTE]
Feel free. I wish I had thought of it myself, but I found it in a list of gay slang terms. I’m very happy with it though; it’s the first label I’ve felt comfortable applying to myself. I wish I didn’t need a label at all, but out society is obsessed with them.
Heterosexual female. Relationship that later was a friends with benefits thing, he was 11 years my senior. When I was 25 I dated a guy for a while who was 52.
Hetro female. When I was 21 I dated a guy who was 34 (so I guess that would be 13 years).
We broke up because he was too immature. That sounds stupid now, but thinking back - nope, he was just too immature.
I wonder what he’s like at 46. Probably still too immature.
female, straight. I only dated three guys within 5 years of my age and I married one of them.
When I was 17 I dated a 34 year old, though I think the biggest gap was when I dated one of my professors; I was about 20 and he was in his middle 50s I would say. Well, I never asked for his driver’s license. My dad was really annoyed, and prof insisted on meeting him. Which I thought was suicidal.
They still go fishing together though the relationship was as fleeting as you might expect.
I’m male. When I was 24, I had sex with a 42 year old woman. She was a friend of a guy I worked for, and I was also pretty good friends with her.
But, we weren’t in a relationship or anything.
Straight female. My first husband and I got married when I was 25 and he was 49. My second and final husband and I got married a few months ago; I’m 35 and he just turned 54.
A twenty year difference is (I think) the greatest age gap for me. I met her when I was thirty and she was fifty.
When I was thirteen-fourteen I systematically hit on every adult woman that came into my perceptual field. There was one woman I hooked up with a few times that was probably in her late thirties, so she probably has a slight edge, there. Can’t be sure, though.
In the other direction, had a romantic relationship with a nineteen-year-old that started in '99, when I was twenty-nine – and a stupid hook-up a few weeks ago with a twenty-year-old. (I’m thirty-five now.)