Older Female/Younger Male Relationship

by AwAiSThEPhEnOm | created - 26 Jul 2012 | updated - 21 Aug 2013 | Public
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1. Summer of '42 (1971)

R | 104 min | Comedy, Drama, Romance

During his summer vacation on Nantucket Island in 1942, a youth eagerly awaiting his first sexual encounter finds himself developing an innocent love for a young woman awaiting news on her soldier husband's fate in WWII.

Director: Robert Mulligan | Stars: Jennifer O'Neill, Gary Grimes, Jerry Houser, Oliver Conant

Votes: 6,632

2. The Rebound (2009)

R | 95 min | Comedy, Romance

In New York City, a single mom captivates her new neighbor, a much younger man.

Director: Bart Freundlich | Stars: Catherine Zeta-Jones, Justin Bartha, Andrew Cherry, Kelly Gould

Votes: 44,349

3. Prime (2005)

PG-13 | 105 min | Comedy, Drama, Romance

58 Metascore

A career driven professional from Manhattan is wooed by a young painter, who also happens to be the son of her psychoanalyst.

Director: Ben Younger | Stars: Uma Thurman, Meryl Streep, Bryan Greenberg, Jon Abrahams

Votes: 38,329 | Gross: $22.83M

4. The Trotsky (2009)

Not Rated | 120 min | Comedy, Drama

59 Metascore

A Montreal high school student who believes he is the reincarnation of Leon Trotsky starts a revolution against apathy among his fellow students.

Director: Jacob Tierney | Stars: Liane Balaban, Jay Baruchel, Taylor Baruchel, Dan Beirne

Votes: 5,558

5. Y Tu Mamá También (2001)

R | 106 min | Drama

88 Metascore

In Mexico, two teenage boys and an attractive older woman embark on a road trip and learn a thing or two about life, friendship, sex, and each other.

Director: Alfonso Cuarón | Stars: Maribel Verdú, Gael García Bernal, Daniel Giménez Cacho, Ana López Mercado

Votes: 108,066 | Gross: $13.62M

6. The Reader (2008)

R | 124 min | Drama, Romance

58 Metascore

Post-WWII Germany: Nearly a decade after his affair with an older woman came to a mysterious end, law student Michael Berg re-encounters his former lover as she defends herself in a war-crime trial.

Director: Stephen Daldry | Stars: Kate Winslet, Ralph Fiennes, Bruno Ganz, Jeanette Hain

Votes: 219,119 | Gross: $34.19M

7. Harold and Maude (1971)

PG | 91 min | Comedy, Drama, Romance

62 Metascore

Young, rich, and obsessed with death, Harold finds himself changed forever when he meets lively septuagenarian Maude at a funeral.

Director: Hal Ashby | Stars: Ruth Gordon, Bud Cort, Vivian Pickles, Cyril Cusack

Votes: 65,854

8. Meet Monica Velour (2010)

R | 98 min | Comedy, Drama, Romance

51 Metascore

When an awkward teen meets his favorite porn star, whose career peaked in the '80s, an unexpected friendship follows as the young man gets a glimpse inside Monica Velour's current life as a single mom struggling to make ends meet.

Director: Keith Bearden | Stars: Kim Cattrall, Dustin Ingram, Brian Dennehy, Jee Young Han

Votes: 2,106 | Gross: $0.03M

9. Womb (2010)

Not Rated | 111 min | Drama, Romance, Sci-Fi

48 Metascore

A woman's consuming love forces her to bear the clone of her dead beloved. From his infancy to manhood, she faces the unavoidable complexities of her controversial decision.

Director: Benedek Fliegauf | Stars: Eva Green, Matt Smith, Lesley Manville, Peter Wight

Votes: 12,579

10. Class (1983)

R | 98 min | Comedy, Drama, Romance

33 Metascore

A young man in private school spends one crazy night out, but soon realizes the woman he hooked up with is not who he expected.

Director: Lewis John Carlino | Stars: Jacqueline Bisset, Rob Lowe, Andrew McCarthy, Cliff Robertson

Votes: 8,878

11. Malena (2000)

R | 108 min | Comedy, Drama, Romance

54 Metascore

Amidst the war climate, a teenage boy discovering himself becomes love-stricken by Malèna, a sensual woman living in a small, narrow-minded Italian town.

Director: Giuseppe Tornatore | Stars: Monica Bellucci, Giuseppe Sulfaro, Luciano Federico, Matilde Piana

Votes: 81,018 | Gross: $3.43M

12. The Graduate (1967)

PG | 106 min | Comedy, Drama, Romance

83 Metascore

A disillusioned college graduate finds himself torn between his older lover and her daughter.

Director: Mike Nichols | Stars: Dustin Hoffman, Anne Bancroft, Katharine Ross, William Daniels

Votes: 239,709 | Gross: $104.95M

13. Broken English (2007)

PG-13 | 93 min | Comedy, Drama, Romance

61 Metascore

Nora Wilder is freaking out. Everyone around her is in a relationship, is married, or has children. Nora is in her thirties, alone with job she's outgrown and a mother who constantly ... See full summary »

Director: Zoe R. Cassavetes | Stars: Parker Posey, Melvil Poupaud, Gena Rowlands, Drea de Matteo

Votes: 5,928 | Gross: $0.96M

14. 40 Carats (1973)

PG | 110 min | Comedy, Romance

Forty year old Norwegian-American divorcée Ann Stanley owns her own Manhattan based real estate agency specializing in upscale Manhattan apartments. She lives with her seventeen year old ... See full summary »

Director: Milton Katselas | Stars: Liv Ullmann, Edward Albert, Gene Kelly, Binnie Barnes

Votes: 569

15. Being Julia (2004)

R | 104 min | Comedy, Drama, Romance

65 Metascore

Set in '30s London, the film involves stage actors and their experiences with love and revenge.

Director: István Szabó | Stars: Annette Bening, Michael Gambon, Maury Chaykin, Jeremy Irons

Votes: 11,600 | Gross: $7.74M

16. A Tiger's Tale (1987)

R | 97 min | Comedy, Drama

A young man falls for his girlfriend's mother.

Director: Peter Douglas | Stars: Ann-Margret, C. Thomas Howell, Charles Durning, Kelly Preston

Votes: 464

17. Bull Durham (1988)

R | 108 min | Comedy, Romance, Sport

73 Metascore

A fan who has an affair with one minor-league baseball player each season meets an up-and-coming pitcher and the experienced catcher assigned to him.

Director: Ron Shelton | Stars: Kevin Costner, Susan Sarandon, Tim Robbins, Trey Wilson

Votes: 44,120 | Gross: $50.89M

18. Cougar Club (2007)

R | 93 min | Comedy

2 friends graduate college and start at a law firm. Hogan is into cougars. Spence needs his employer's recommendation for Yale Law so being with his wife isn't smart. He helps Hogan start Cougar Club.

Director: Christopher Duddy | Stars: Jason Jurman, Warren Kole, Joe Mantegna, Kaley Cuoco

Votes: 3,271

19. Belle maman (1999)

102 min | Comedy

On his wedding day, Antoine falls madly in love with Léa, his mother-in-law.

Director: Gabriel Aghion | Stars: Catherine Deneuve, Vincent Lindon, Mathilde Seigner, Line Renaud

Votes: 816

20. Big (1988)

PG | 104 min | Comedy, Drama, Fantasy

73 Metascore

After wishing to be made big, a teenage boy wakes the next morning to find himself mysteriously in the body of an adult.

Director: Penny Marshall | Stars: Tom Hanks, Elizabeth Perkins, Robert Loggia, John Heard

Votes: 181,200 | Gross: $114.97M

21. Breakfast at Tiffany's (1961)

Not Rated | 115 min | Comedy, Drama, Romance

76 Metascore

A young New York socialite becomes interested in a young man who has moved into her apartment building, but her past threatens to get in the way.

Director: Blake Edwards | Stars: Audrey Hepburn, George Peppard, Patricia Neal, Buddy Ebsen

Votes: 152,814

22. Chéri (2009)

R | 86 min | Comedy, Drama, Romance

63 Metascore

The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.

Director: Stephen Frears | Stars: Michelle Pfeiffer, Rupert Friend, Kathy Bates, Frances Tomelty

Votes: 10,080 | Gross: $2.71M

23. Milf (2010 Video)

Unrated | 88 min | Comedy

A group of nerdy college guys who can't seem to connect with girls their own age discover the excitement of hooking up with sexy older women.

Director: Scott Wheeler | Stars: Jack Cullison, Philip Marlatt, Joseph Booton, Ramon Camacho

Votes: 5,063

24. The Door in the Floor (2004)

R | 111 min | Comedy, Drama

67 Metascore

A writer's young assistant becomes both pawn and catalyst in his boss's disintegrating household.

Director: Tod Williams | Stars: Jeff Bridges, Kim Basinger, Jon Foster, Elle Fanning

Votes: 14,766 | Gross: $3.84M

25. Crush (I) (2001)

R | 108 min | Comedy, Romance, Drama

37 Metascore

Three female friends behave badly.

Director: John McKay | Stars: Andie MacDowell, Imelda Staunton, Anna Chancellor, Kenny Doughty

Votes: 3,523 | Gross: $1.08M

26. Diva (1981)

R | 117 min | Thriller

Two tapes, two Parisian mob killers, one corrupt policeman, an opera fan, a teenage thief, and the coolest philosopher ever filmed. All these characters twist their way through an intricate and stylish French language thriller.

Director: Jean-Jacques Beineix | Stars: Wilhelmenia Fernandez, Frédéric Andréi, Richard Bohringer, Thuy An Luu

Votes: 10,969 | Gross: $0.11M

27. The Private Lives of Elizabeth and Essex (1939)

Approved | 106 min | Biography, Drama, History

A depiction of the love/hate relationship between Queen Elizabeth I and Robert Devereux, the Earl of Essex.

Director: Michael Curtiz | Stars: Bette Davis, Errol Flynn, Olivia de Havilland, Donald Crisp

Votes: 4,605

28. Far from Heaven (2002)

PG-13 | 107 min | Drama

84 Metascore

In 1950s Connecticut, a housewife faces a marital crisis and mounting racial tensions in the outside world.

Director: Todd Haynes | Stars: Julianne Moore, Dennis Quaid, Dennis Haysbert, Patricia Clarkson

Votes: 41,561 | Gross: $15.85M

29. The Good Girl (2002)

R | 93 min | Drama, Romance

71 Metascore

A discount store clerk strikes up an affair with a stock boy who considers himself the incarnation of Holden Caulfield.

Director: Miguel Arteta | Stars: Jennifer Aniston, Jake Gyllenhaal, Deborah Rush, Mike White

Votes: 41,535 | Gross: $14.02M

30. Sunset Blvd. (1950)

Not Rated | 110 min | Drama, Film-Noir

A screenwriter develops a dangerous relationship with a faded film star determined to make a triumphant return.

Director: Billy Wilder | Stars: William Holden, Gloria Swanson, Erich von Stroheim, Nancy Olson

Votes: 181,993

31. How Stella Got Her Groove Back (1998)

R | 124 min | Comedy, Drama, Romance

56 Metascore

Stella is a highly successful, forty-something San Francisco stock broker who is persuaded by her colorful New York girlfriend Delilah to take a well deserved, first-class vacation to ... See full summary »

Director: Kevin Rodney Sullivan | Stars: Angela Bassett, Taye Diggs, Whoopi Goldberg, Regina King

Votes: 6,388 | Gross: $37.67M

32. Heading South (2005)

Unrated | 108 min | Drama

73 Metascore

Three female tourists have their eyes opened while visiting the poverty-stricken and dangerous world of 1980s Haiti.

Director: Laurent Cantet | Stars: Charlotte Rampling, Karen Young, Louise Portal, Ménothy Cesar

Votes: 2,603 | Gross: $0.90M

33. Impromptu (1991)

PG-13 | 107 min | Biography, Comedy, Music

In 1830s France, pianist/composer Frédéric Chopin is pursued romantically by the determined, individualistic woman who uses the name George Sand.

Director: James Lapine | Stars: Judy Davis, Hugh Grant, Mandy Patinkin, Bernadette Peters

Votes: 4,422 | Gross: $4.08M

34. In Praise of Older Women (1978)

R | 110 min | Comedy, Drama, Romance

Andras Vajda grows up in a turbulent, war-torn Hungary, where he procures local girls for the occupying G.I.'s during World War II. Disappointed by girls of his age, he meets Maya, a ... See full summary »

Director: George Kaczender | Stars: Tom Berenger, Karen Black, Susan Strasberg, Helen Shaver

Votes: 562

35. I Could Never Be Your Woman (2007)

PG-13 | 97 min | Comedy, Drama, Romance

A mother falls for a younger man while her daughter falls in love for the first time. Mother Nature messes with their fates.

Director: Amy Heckerling | Stars: Michelle Pfeiffer, Paul Rudd, Saoirse Ronan, Tracey Ullman

Votes: 16,346

36. Notes on a Scandal (2006)

R | 92 min | Crime, Drama, Romance

73 Metascore

A veteran high school teacher befriends a younger art teacher, who is having an affair with one of her 15-year-old students. However, her intentions with this new "friend" also go well beyond platonic friendship.

Director: Richard Eyre | Stars: Cate Blanchett, Judi Dench, Andrew Simpson, Tom Georgeson

Votes: 71,480 | Gross: $17.51M

37. In the Bedroom (2001)

R | 130 min | Crime, Drama

86 Metascore

A New England couple's college-aged son dates an older woman who has two small children and an unwelcome ex-husband.

Director: Todd Field | Stars: Tom Wilkinson, Sissy Spacek, Nick Stahl, Marisa Tomei

Votes: 35,534 | Gross: $35.93M

38. Life as a House (2001)

R | 125 min | Drama

45 Metascore

When a man is diagnosed with terminal cancer, he takes custody of his misanthropic teenage son, for whom quality time means getting high, engaging in small-time prostitution, and avoiding his father.

Director: Irwin Winkler | Stars: Hayden Christensen, Kevin Kline, Kristin Scott Thomas, Jena Malone

Votes: 41,814 | Gross: $15.65M

39. Losin' It (1983)

R | 100 min | Comedy, Drama

51 Metascore

Set in 1965, four rowdy teenage guys travel to Tijuana, Mexico for a night of partying when they are joined by a heartbroken housewife who is in town seeking a quick divorce.

Director: Curtis Hanson | Stars: Tom Cruise, Jackie Earle Haley, John Stockwell, John P. Navin Jr.

Votes: 3,802 | Gross: $1.25M

40. Lovely & Amazing (2001)

R | 91 min | Comedy, Drama, Romance

75 Metascore

Self-esteem and insecurity are at the heart of this comedy about the relationship between a mother and her three confused daughters.

Director: Nicole Holofcener | Stars: Catherine Keener, Brenda Blethyn, Troy Ruptash, Emily Mortimer

Votes: 6,578 | Gross: $4.19M

41. Meeting Venus (1991)

PG-13 | 119 min | Comedy, Drama, Romance

A deliciously biting satire about both the world of Grand Opera and United Europe. A Hungarian conductor (Arestrup) attempts to mount a bold new production of Richard Wagner's "Tannhäuser" ... See full summary »

Director: István Szabó | Stars: Glenn Close, Niels Arestrup, Kiri Te Kanawa, René Kollo

Votes: 1,149 | Gross: $1.00M

42. The Mother (2003)

R | 112 min | Drama, Romance

72 Metascore

A woman has a passionate affair with a man half her age, who is also sleeping with her daughter.

Director: Roger Michell | Stars: Anne Reid, Daniel Craig, Anna Wilson-Jones, Peter Vaughan

Votes: 3,799 | Gross: $1.06M

43. P.S. (2004)

R | 97 min | Comedy, Drama, Fantasy

55 Metascore

An unfulfilled divorced woman gets the chance to relive her past when she meets a young man who appears to be her high school sweetheart who died many years before.

Director: Dylan Kidd | Stars: Laura Linney, Topher Grace, Marcia Gay Harden, Gabriel Byrne

Votes: 5,804 | Gross: $0.18M

44. The Love Letter (1999)

PG-13 | 88 min | Comedy, Drama, Romance

The power of words and images to open hearts. Helen runs, miles a day, to burn off energy: she's an emotional celibate. Going through the post at her shop, she finds a romantic and poetic ... See full summary »

Director: Peter Ho-Sun Chan | Stars: Kate Capshaw, Tom Everett Scott, Tom Selleck, Blythe Danner

Votes: 3,899 | Gross: $8.28M

45. A Night in Heaven (1983)

R | 83 min | Drama, Romance

A married college professor begins a torrid affair with her failing student, who secretly moonlights as a late-night strip-club dancer.

Director: John G. Avildsen | Stars: Christopher Atkins, Lesley Ann Warren, Robert Logan, Deborah Rush

Votes: 1,083 | Gross: $5.56M

46. The Pallbearer (1996)

PG-13 | 98 min | Comedy, Romance

A young man's life is thrown into a loop when he is asked to be a pallbearer for the funeral of a classmate he doesn't remember, and his old high school crush temporarily returns to town.

Director: Matt Reeves | Stars: David Schwimmer, Gwyneth Paltrow, Michael Rapaport, Toni Collette

Votes: 7,413 | Gross: $5.61M

47. Private Lessons (1981)

R | 87 min | Comedy

34 Metascore

An immigrant housemaid seduces a 15-year-old boy and later fakes her own death as part of his chauffeur's blackmail plot. Troubles arise when the two start to fall in love.

Director: Alan Myerson | Stars: Sylvia Kristel, Howard Hesseman, Eric Brown, Patrick Piccininni

Votes: 3,002 | Gross: $26.28M

48. Water for Elephants (2011)

PG-13 | 120 min | Drama, Romance

52 Metascore

Set in the 1930s, a former veterinary student takes a job in a travelling circus and falls in love with the ringmaster's wife.

Director: Francis Lawrence | Stars: Robert Pattinson, Reese Witherspoon, Christoph Waltz, Paul Schneider

Votes: 106,391 | Gross: $58.71M

49. Rushmore (1998)

R | 93 min | Comedy, Drama

7.7