Older Woman Younger Man Relationship Movies

  • 1988
    Kung-Fu Master!

    Kung-Fu Master!

    Kung-Fu Master!

    6.31988HD

    A lonely 40-year old woman finds herself shattering taboos by falling in love with the 14-year old Julien – but is it romance, or a desperate...

    Kung-Fu Master!
  • 1996
    A Friend's Betrayal

    A Friend's Betrayal

    A Friend's Betrayal

    5.61996HD

    Old feelings of betrayal resurface, renewing a bitter rift between two girlfriends when one learns that the other seduced her son.

    A Friend's Betrayal
  • 2016
    In Bed with Victoria

    In Bed with Victoria

    In Bed with Victoria

    5.92016HD

    Victoria is a thirty-something divorced lawyer who's struggling to raise her two daughters. She is canny and cynical but on the verge of an emotional...

    In Bed with Victoria
  • 1989
    Sweet Bird of Youth

    Sweet Bird of Youth

    Sweet Bird of Youth

    5.51989HD

    Tennessee William’s masterful melodrama about an aging movie star who, appalled by her own image on the screen, flees from her movie premiere...

    Sweet Bird of Youth
  • 1959
    Violent Summer

    Violent Summer

    Violent Summer

    7.21959HD

    Summer, 1943: wealthy youth in the Riccione district of Rimini play while the war gets closer. Carlo Caremoli, a young man who follows the crowd, has...

    Violent Summer
  • 1973
    Love and Pain and the Whole Damn Thing

    Love and Pain and the Whole Damn Thing

    Love and Pain and the Whole Damn Thing

    6.11973HD

    While bicycling through the Spanish countryside, Walter, the aimless young son of a doctor, makes the acquaintance of proper, middle-aged, clumsy and...

    Love and Pain and the Whole Damn Thing
  • 2002
    Crush

    Crush

    Crush

    5.72002HD

    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...

    Crush
  • 1996
    August

    August

    August

    4.31996HD

    Set in 1890s North Wales over a long, hot August weekend, the Victorian calm of a household is suddenly upset with the arrival of a London couple who...

    August
  • 2019
    All These Small Moments

    All These Small Moments

    All These Small Moments

    6.52019HD

    A teenage boy's infatuation with a woman he sees on the bus further complicates his already tumultuous adolescence.

    All These Small Moments
  • 1973
    40 Carats

    40 Carats

    40 Carats

    5.71973HD

    After an overnight fling with a man nearly 20 years her junior while vacationing in Greece, Ann Stanley returns to New York assuming she'll never see...

    40 Carats
  • 1992
    Oh, What a Night

    Oh, What a Night

    Oh, What a Night

    4.51992HD

    During the summer of 1955, seventeen-year-old Eric Hansen embarks on a journey in his new town, a journey which will change his life forever.

    Oh, What a Night
  • 2001
    Absolutely Fabulous

    Absolutely Fabulous

    Absolutely Fabulous

    4.92001HD

    Middle-aged best friends Eddie and Patsy live in an endless haze of drugged, drunken selfishness. The duo leave no impulse unenacted and no lust...

    Absolutely Fabulous
  • 2018
    When Love Digs a Hole

    When Love Digs a Hole

    When Love Digs a Hole

    7.52018HD

    A troubled teenager falls in love with Florence, his 73-year-old neighbor.

    When Love Digs a Hole
  • 1985
    The Big Bet

    The Big Bet

    The Big Bet

    51985HD

    A high school student obsessed with sex tries to seduce both his beautiful older neighbor and the shy new girl in school over a bet, only to end up...

    The Big Bet
  • 2007
    Punish Me

    Punish Me

    Punish Me

    4.72007HD

    Angelina Maccarone's intense drama deals with the obsessive relationship between a confused teenager and an elder woman. Elsa Seifert successfully...

    Punish Me
  • 1971
    There's Always Vanilla

    There's Always Vanilla

    There's Always Vanilla

    4.61971HD

    A young man returns home to Pittsburgh and moves in with an older woman, on whom he begins to rely on for emotional and financial support.

    There's Always Vanilla
  • 2025
    Chaperone

    Chaperone

    Chaperone

    6.32025HD

    Set in rural Hawai’i and featuring an entirely AANHPI cast, Chaperone follows Misha, an unambitious 29-year-old woman who finds a dangerous...

    Chaperone
  • 1976
    The Summer I Turned 15

    The Summer I Turned 15

    The Summer I Turned 15

    5.51976HD

    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...

    The Summer I Turned 15
  • 1998
    Last Night

    Last Night

    Last Night

    6.61998HD

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

    Last Night
  • 2025
    My Love Story with Yamada-kun at Lv999

    My Love Story with Yamada-kun at Lv999

    My Love Story with Yamada-kun at Lv999

    6.72025HD

    Akane Kinoshita is a university student, who was recently dumped by her ex-boyfriend. She is still heart broken by the rejection. She meets high...

    My Love Story with Yamada-kun at Lv999