Older Female/Younger Male Relationshipby 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.
3. Prime (2005)
PG-13 | 105 min | Comedy, Drama, Romance
A career driven professional from Manhattan is wooed by a young painter, who also happens to be the son of her psychoanalyst.
Votes: 38,329 | Gross: $22.83M
4. The Trotsky (2009)
Not Rated | 120 min | Comedy, Drama
A Montreal high school student who believes he is the reincarnation of Leon Trotsky starts a revolution against apathy among his fellow students.
5. Y Tu Mamá También (2001)
R | 106 min | Drama
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.
Votes: 108,066 | Gross: $13.62M
6. The Reader (2008)
R | 124 min | Drama, Romance
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.
Votes: 219,119 | Gross: $34.19M
8. Meet Monica Velour (2010)
R | 98 min | Comedy, Drama, Romance
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.
Votes: 2,106 | Gross: $0.03M
9. Womb (2010)
Not Rated | 111 min | Drama, Romance, Sci-Fi
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.
11. Malena (2000)
R | 108 min | Comedy, Drama, Romance
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.
Votes: 81,018 | Gross: $3.43M
13. Broken English (2007)
PG-13 | 93 min | Comedy, Drama, Romance
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 »
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 »
17. Bull Durham (1988)
R | 108 min | Comedy, Romance, Sport
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.
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.
21. Breakfast at Tiffany's (1961)
Not Rated | 115 min | Comedy, Drama, Romance
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.
22. Chéri (2009)
R | 86 min | Comedy, Drama, Romance
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.
Votes: 10,080 | Gross: $2.71M
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.
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.
31. How Stella Got Her Groove Back (1998)
R | 124 min | Comedy, Drama, Romance
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 »
Votes: 6,388 | Gross: $37.67M
33. Impromptu (1991)
PG-13 | 107 min | Biography, Comedy, Music
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 »
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.
36. Notes on a Scandal (2006)
R | 92 min | Crime, Drama, Romance
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.
Votes: 71,480 | Gross: $17.51M
38. Life as a House (2001)
R | 125 min | Drama
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.
Votes: 41,814 | Gross: $15.65M
39. Losin' It (1983)
R | 100 min | Comedy, Drama
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.
Votes: 3,802 | Gross: $1.25M
40. Lovely & Amazing (2001)
R | 91 min | Comedy, Drama, Romance
Self-esteem and insecurity are at the heart of this comedy about the relationship between a mother and her three confused daughters.
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 »
Votes: 1,149 | Gross: $1.00M
43. P.S. (2004)
R | 97 min | Comedy, Drama, Fantasy
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.
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 »
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.
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.
Votes: 7,413 | Gross: $5.61M
47. Private Lessons (1981)
R | 87 min | Comedy
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.
Votes: 3,002 | Gross: $26.28M
48. Water for Elephants (2011)
PG-13 | 120 min | Drama, Romance
Set in the 1930s, a former veterinary student takes a job in a travelling circus and falls in love with the ringmaster's wife.
Votes: 106,391 | Gross: $58.71M
49. Rushmore (1998)
R | 93 min | Comedy, Drama