The May-December Romance

On Flavorwire they’re listing their favorite movies about relationships [mostly] between older men and younger women (a type of relationship called the “May-December Romance,” because she is like a blossoming May flower and he is nearing death), and so over here maybe we can do something similar. How much older is the oldest person you’ve dated [slept with/touched/whispered to]? Say it! Sayyy ittt, it doesn’t even matter, no one’s listening, who cares, why are you acting all weird? (Alternately, the youngest? Let’s stay up all night and never go to sleep.)