Knew a guy in high school that met his girlfriend when he was in 11th and she was in 7th. Used to make jokes about him because of it. Kind of an odd couple even without the age difference. His personality was incredibly boring and his voice was monotone. The one time I met her, she was acting like an annoying hyperactive little kid (rolling on the floor, talking too fast, looking for from everyone etc).
They were together until he went away for college then she cheated on him.
The only other major example I can think of is I knew another guy who was about 35 and he started hanging out with a lot of teenage girls who were around 17-19 so he was deliberately dancing around the age of consent line.
Now the girls he was hanging out with were of course all on the wild side (and probably had daddy issues) so they weren't really innocent themselves, but my dad and I kept warning him if he continued down this path he was going to end up getting himself into a whole mess of trouble.
And that's exactly what happened.
He ended up pissing off one of these girls severely enough that she accused him of rape. What actually happened is they went to a party, she had sex with two guys in the bathroom there, he took her back to his place then they had sex. They got into an argument the next morning and she wanted him to take her back home. He said she could get home herself and basically she was stuck at his house until he decided to finally take her back home.
At that point I guess it was when she decided to get revenge him and accuse him of rape. At first he was really worried about it, but then he figured she was bluffing or he just didn't think he was going to get into trouble because there was "no proof" of any crime so he just continued with his life as normal rather than doing the smart thing like hiring a lawyer right away (or for a more criminal mindset, flee the area).
Well eventually the police busted him SWAT team style a couple months later when he was leaving his house to go to work. He was even on the damn news since he got taken in by this really overzealous cop who saw himself as cleaning up the streets of sexual predators.
Didn't help either that the girl was 17 and came from a fairly wealthy family, while he looked like some 35 year old pervert that snatched her off the street. He had to sell most of his possessions just to raise money for a competent lawyer. He was in jail until the trial where he had to ultimately plead guilty to sexual misconduct in the 1st degree or something like that.
He got six years in prison. He's out, but now he's got a permanent record as a sex offender.
As for the girl, last time heard anything about her was a few months after the guy I mentioned went to prison. She was at a bar my dad was working at the time and she started hitting on him. He told her to get the hell away and had her thrown out of the bar telling the owner that she was under the drinking age anyway.
The morale of the story is "If you're gonna mess around with jailbait, you're gonna have a bad time."