Older Woman Younger Man Relationship Movies

An older woman shows a high schooler how to woo a girl and win a bet with a bully.

Beautiful, sophisticated women are all over Oscar Grubman. He is sensitive and compassionate, speaks French fluently, is passionate about Voltaire,...

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...

Liverpool, 1978: What starts as a vibrant affair between a legendary femme-fatale, the eccentric Academy Award-winning actress Gloria Grahame, and...

This movie is a sequel to the saga of movies about 3 guys in the middle of the 50's during their sex urges and other funny incidents.

After spending a decade in a failed relationship, successful couples’ therapist Ally is turning 40 and is pushed, kicking and screaming, by her...

Dear Sidewalk tells the story of Gardner, a 24 year old mail-carrier, who is struggling to contend with his identity as his quarter-life crisis is in...

On the beaches of Kenya they’re known as "Sugar Mamas" —European women who seek out African boys selling love to earn a living. Teresa, a...

Two different social classes collide when Cary Scott, a wealthy upper-class widow, falls in love with her much younger and down-to-earth gardener,...

A retired auto manufacturer and his wife take a long-planned European vacation only to find that they want very different things from life.

Tells the tale of three buddies in their 20's whose love-lives are in shambles. They go to Aspen to pursue the booming trend of dating cougars: hot...

For Tobe, a nerdy, horny, frizzy-haired cineaste who doesn't quite fit in with the average contemporary teen, the pinnacle of womanhood is Monica...

Waldemar Nods, a young man from Suriname, meets the older Dutch woman Rika van der Lans and they fall in love. In pre-WWII Netherlands they could not...

Anna is 60 and her acting heyday is now behind her. She lives on her own but has a friend and confidant in her downstairs neighbour Michel, who is...

The story Peter is telling the about a special summer, when he is invited over to summer holiday from bickering parents, to his aunt and uncle in the...

Martin, who believes himself to be a vampire, goes to live with his elderly and hostile cousin in a small Pennsylvania town where he tries to redeem...

In the Paris of the 1910s, brash young sculptor Henri Gaudier begins a creative partnership with an older writer, Sophie Brzeska. Though the couple...

Handsome but backward gardener Tim Melville has a new woman in his life. She is Mary, his widowed employer, a woman who had given up on love until...

Various citizens of Toronto anxiously await the end of the world, which is occurring at the stroke of midnight on New Year's Day.

Cal, a young man on the fringes of the IRA, falls in love with Marcella, a Catholic woman whose husband, a Protestant policeman, was killed one year...