Older Woman Younger Man Relationship Movies

  • 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
  • 1971
    The Road Builder

    The Road Builder

    The Road Builder

    6.31971HD

    The dreary existence of middle-aged spinster Maura Prince takes an unexpected turn with the arrival of young handyman Billy Jarvis, but there may be...

    The Road Builder
  • 2007
    Lezioni di volo

    Lezioni di volo

    Lezioni di volo

    6.32007HD

    A pair of teen friends – known as "Chicken & Curry" because they are virtually inseparable – fail their high school finals and try to...

    Lezioni di volo
  • 1983
    The First Time

    The First Time

    The First Time

    51983HD

    A young film student pursues a woman while studying under a bizarre, eccentric film professor.

    The First Time
  • 2017
    Tomato Red

    Tomato Red

    Tomato Red

    6.42017HD

    When small town drifter Sammy Barlach drives into Venus Holler in search for his next cold beer and the bunch that'll have him, he gets a lot more...

    Tomato Red
  • 2013
    Dear Sidewalk

    Dear Sidewalk

    Dear Sidewalk

    7.12013HD

    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...

    Dear Sidewalk
  • 2000
    Desire

    Desire

    Desire

    3.52000HD

    An affair between a pianist and a teacher begins to disintegrate when girls from her school turn up missing.

    Desire
  • 1957
    Guest at One's Own Home

    Guest at One's Own Home

    Guest at One's Own Home

    81957HD

    Eva Dahl, a doctor's wife, starts an affair with a younger man.

    Guest at One's Own Home
  • 1996
    Mary & Tim

    Mary & Tim

    Mary & Tim

    6.81996HD

    Another adaptation of the novel "Tim", about the love that develops between a mentally challenged young man and the older, lonely widow who takes him...

    Mary & Tim
  • 2024
    Paalum Pazhavum

    Paalum Pazhavum

    Paalum Pazhavum

    6.52024HD

    After a woman falls for a younger man, the couple find themselves facing discrimination due to their age gap.

    Paalum Pazhavum
  • 2013
    Present Perfect Continuous Tense

    Present Perfect Continuous Tense

    Present Perfect Continuous Tense

    62013HD

    Jing is a teenager who starts dating Eiam, a woman who is 20 years older than him. Things go well at the beginning but when Eiam turns 40 and Jing...

    Present Perfect Continuous Tense
  • 1971
    Romance

    Romance

    Romance

    4.61971HD

    Love story between a young man and a married woman. She's married to a businessman who's neglecting her. She would like to leave him but she's afraid...

    Romance
  • 1998
    El niño que enloqueció de amor

    El niño que enloqueció de amor

    El niño que enloqueció de amor

    81998HD

    A young boy becomes infatuated towards an older woman. TV movie based on Eduardo Barrios's novel of the same title.

    El niño que enloqueció de amor
  • 1986
    A Seaside Story

    A Seaside Story

    A Seaside Story

    5.21986HD

    On a weekend trip to the seaside town of Lyme Regis, two seventeen-year-old boys - Sam with an interest in ecology and Martin with an interest in...

    A Seaside Story
  • 2012
    Blissful Lies

    Blissful Lies

    Blissful Lies

    02012HD

    Blissful Lies examines the close ties and bonds between a group of 5 college-aged people who find that the limits of their relationships are tested...

    Blissful Lies
  • 1992
    Sinungaling Mong Puso

    Sinungaling Mong Puso

    Sinungaling Mong Puso

    101992HD

    An endearing romantic drama that tells of a very curious affair between Clara, an older woman and Jason, a young unhappily married boy. In between...

    Sinungaling Mong Puso
  • 2020
    Boys & Toys

    Boys & Toys

    Boys & Toys

    02020HD

    30-something Abby hits on a younger guy at a bar. Things get awkward when it turns out she already knows him.

    Boys & Toys
  • 1970
    In the Company of Strangers

    In the Company of Strangers

    In the Company of Strangers

    01970HD

    A woman trapped in a loveless marriage finds passion with a younger man from a different social background. Their secret relationship unfolds against...

    In the Company of Strangers