May-December
by cesarbs | created - 05 Mar 2012 | updated - 05 Mar 2012 | Public- Instant Watch Options
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1. 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: 50,228
2. Flirting with Forty (2008 TV Movie)
TV-PG | 87 min | Comedy, Drama, Romance
A divorced mother approaching her 40th birthday falls for a younger man while on vacation.
Director: Mikael Salomon | Stars: Heather Locklear, Robert Buckley, Vanessa Williams, Cameron Bancroft
Votes: 2,776
3. 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 Jamaica.
Director: Kevin Rodney Sullivan | Stars: Angela Bassett, Taye Diggs, Whoopi Goldberg, Regina King
Votes: 8,332 | Gross: $37.67M
4. Goodbye Again (1961)
Not Rated | 120 min | Drama, Romance
A successful business woman, dissatisfied with her current, philandering lover, starts an affair with a much younger man.
Director: Anatole Litvak | Stars: Ingrid Bergman, Yves Montand, Anthony Perkins, Jessie Royce Landis
Votes: 3,122
5. Crush (I) (2001)
R | 108 min | Comedy, Drama, Romance
Three 40-something women in a small English town meet weekly for a ritual of gin, cigarettes, and sweets -- and swap stories arguing which of them has the most pathetic love life. Kate is ... See full summary »
Director: John McKay | Stars: Andie MacDowell, Imelda Staunton, Anna Chancellor, Kenny Doughty
Votes: 3,957 | Gross: $1.08M
6. Tim (1979)
Not Rated | 109 min | Drama, Romance
A somewhat mentally handicapped 20-year-old man works as a laborer, but everyone abuses his naiveté. A nice 40-year-old American woman hires him one day and they become close. However, the town and his family see her as predatory.
Director: Michael Pate | Stars: Piper Laurie, Mel Gibson, Alwyn Kurts, Pat Evison
Votes: 3,688
7. All That Heaven Allows (1955)
Passed | 89 min | Drama, Romance
An upper-class widow falls in love with a much younger, down-to-earth nurseryman, much to the disapproval of her children and criticism of her country club peers.
Director: Douglas Sirk | Stars: Jane Wyman, Rock Hudson, Agnes Moorehead, Conrad Nagel
Votes: 16,644
8. 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: 19,465
9. 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.
Director: Dylan Kidd | Stars: Laura Linney, Topher Grace, Marcia Gay Harden, Gabriel Byrne
Votes: 6,547 | Gross: $0.18M
10. 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: 11,602 | Gross: $5.61M
11. 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.
Directors: Alan Myerson, James Fargo | Stars: Sylvia Kristel, Howard Hesseman, Eric Brown, Patrick Piccininni
Votes: 4,267 | Gross: $26.28M
12. White Palace (1990)
R | 103 min | Drama, Romance
Lust turns to love for a 40-ish working-class woman and a 20-ish yuppie adman with little in common.
Director: Luis Mandoki | Stars: Susan Sarandon, James Spader, Jason Alexander, Kathy Bates
Votes: 8,930 | Gross: $17.49M
13. 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.
Director: Stephen Frears | Stars: Michelle Pfeiffer, Rupert Friend, Kathy Bates, Frances Tomelty
Votes: 11,682 | Gross: $2.71M
14. The Proposal (I) (2009)
PG-13 | 108 min | Comedy, Drama, Romance
A pushy boss forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation to Canada.
Director: Anne Fletcher | Stars: Sandra Bullock, Ryan Reynolds, Mary Steenburgen, Craig T. Nelson
Votes: 360,622 | Gross: $163.96M
15. 500 Days of Summer (2009)
PG-13 | 95 min | Comedy, Drama, Romance
After being dumped by the girl he believes to be his soulmate, hopeless romantic Tom Hansen reflects on their relationship to try and figure out where things went wrong and how he can win her back.
Director: Marc Webb | Stars: Zooey Deschanel, Joseph Gordon-Levitt, Geoffrey Arend, Chloë Grace Moretz
Votes: 558,374 | Gross: $32.39M
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