Biggest age differences in dating you know of?

[GordoBarraBJJ]

Friend is 45 his new gf is 23

 

[loyalyolayal]

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.

Dowry was involved.

 

[no fat chicks]

18 n 45, they have a kid now too

 

[KimuraNova]

my friend has a 75 year old father that married (4th marriage) a 35 year old woman and they recently had a baby. my friend has a kid as well that is older than the newly born baby, so the kids uncle is younger than him..
I remember my friend telling me that he has a lot of difficulty communicating with his brother. he told me it basically boils down to him not knowing not to talk yet. he seems to joke around with this stuff but I feel deep down he is really angry with his father and considers him irresponsible.

 

[melvinj0]

Didn't really know her, but my sister's friend use to bang a 55 year old guy when she was 16. He didn't get in any kind of trouble because she claimed she never told him her age, and often used fake ID's when they went out.