The Age Gap

She's a school girl, he's in his 40's. Based on true events.

Something's Gotta Give involved Jack Nicholson dating the daughter of Meryl Streep. He was older than the age of her father. When Jack and Meryl meet, they don't exactly hit it off. But soon Jack has to decide between the two women. In the meantime, Meryl meets a younger man (Keanu Reeves).

Richard Gere and Winona Ryder are in a May-December romance - he's an older womanizer, she's the woman who falls in love with him.

Michael and Sararh. She sleeps with him, gets pregnant so in the future, her son will send his father back in time to meet his mother and conceive their son. But apart from that problem (which is only revealed about half way through the movie, so you won’t care about time travel paradoxes, you’re just thinking how awesome the future will be) they’re perfectly sweet – they make tender sweet love.

Aragorn meets Arwen at the tender age of twenty and immediately falls in love. When Aragorn was born, Arwen was 2680 years old.

Annabelle is a 17 year old Catholic schoolgirl who falls in love with her teacher Simone Bradley. The pushy teenager pursues her until the 30-something year old falls equally in love with Annabelle. Not long after they give in to their lusts their relationship is discovered and Simone is arrested.

Ladyhawke has Rutger Hauer and Michelle Pfeiffer as a love-crossed couple who can never be together, until the curse is lifted. It's set in medieval times. This was a 13 year difference.

A sixteen year old boy falls for a 79 year old who has the same type of spirit as he.

Three 40-something women in a small English town meet weekly for a ritual of gin, cigarettes, and sweets -- and swapped stories arguing which of them has the most pathetic love life. Kate (MacDowell) is headmistress at the local school; her best friends are the town's police chief (Staunton) and a cynical, thrice-divorced doctor (Chancellor). When Kate begins a fling with a handsome younger man (Doughty), less worldly than her friends but passionate and sincere, the other women can't simply be happy for the couple's unusual new romance. In jealousy they promptly take it upon themselves to break up the pair, taking drastic measures which result in unintended outcomes, some happy and some tragic.

Clint Eastwood directing his earlier films... a successful middle-aged man that falls in love with a young and attractive hippie.