Highest-Rated Movies about 'Older Woman-younger Man', Sort by Popularity

Hello, My Name Is Doris (2015), Harold and Maude (1971), Breakfast at Tiffany's (1961), All That Heaven Allows (1955), Another Man's Poison (1951), Hello, My Name Is Doris (2015), Love in Another Town (1997), A Teacher (2013) ... Let's take a look at the ranked list of the best Older Woman-younger Man movies.

#2. Harold and Maude (1971)

Storyline: Young adult Harold Chasen, solitary and friendless by choice, is obsessed with death, this fascination manifesting itself in he staging his own fake suicides, driving a hearse and attending funerals, even of people he doesn't know, all to the chagrin of his exasperated wealthy mother with who he lives. Mrs. Chasen is determined for Harold to be "normal", including she sending him into therapy to deal with his issues and finding him a girlfriend through a computer dating service. It is at a series of funerals that Harold meets Maude, on the cusp of her eightieth birthday, she who too attends funerals of strangers. Unlike Harold, Maude is obsessed with life - her own life to be more precise - she doing whatever she wants to please herself, damned what others may think or how they may be affected. Since she can't take material possessions with her, she is more interested in experiences, with whatever material possessions she has - often "borrowed" without asking - only to further those ...

Plot Keywords: survivor, teenager, mother, quirky, dark, emotional, cemetery ...

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#3. Breakfast at Tiffany's (1961)

Storyline: Paul Varjak - a young wannabe writer and the kept young man of an older woman - Emily Eustace Failenson ays(aka '2E') - and meets Holly Golightly; a flighty Manhattan party girl, who's his neighbour in the brownstone she's set him up in. As Paul find out more about Holly, he begins to feel something for her, and she- always on the make - tries to be the insouciant waif.

Plot Keywords: socialite, writer, wealthy woman, love interest, dreamy, emotional, melodramatic ...

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#4. All That Heaven Allows (1955)

Storyline: Cary Scott is a widow with two grown children. She's been leading a quiet life since her husband died, socializing with a small circle of friends. Her children no longer live with her full-time but come home every weekend. She's not unhappy but also doesn't realize how bored she is. Her friend Sara Warren encourages her to get a television set to keep her company but she doesn't want that either. She develops a friendship with Ron Kirby who owns his own nursery and comes every spring and fall to trim her trees. Ron is much younger than Cary and their friendship soon turns to love. Her circle of friends are surprised that she is seeing such a younger man and she might be prepared to overlook that - Ron certainly doesn't care about the differences in their ages - but when her son and daughter vehemently object, she decides to sacrifice her own feelings for their happiness. Over time however, she realizes that her children will be spending less and less time with her as they pursue their...

Plot Keywords: widow, daughter, neighbor, love interest, emotional, melodramatic, new england ...

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#5. Another Man's Poison (1951)

Storyline: Mystery writer Janet Frobisher lives alone in a dark English country house, when she's not philandering with her secretary's fiancée. At an extremely awkward moment, she has an unwelcome visitor: George Bates, who claims to be the partner in crime of Janet's estranged husband. George insinuates himself into Janet's home and life despite her efforts to get rid of him; the tangled relationships develop into a macabre, murderous cat-and-mouse game.—Rod Crawford <puffinus@u.washington.edu>

Plot Keywords: novelist, veterinarian, husband, secretary, fiancé, mysterious man, tense ...

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#6. Hello, My Name Is Doris (2015)

Storyline: Doris Miller is a shy, eccentric 60-something woman, living alone following the death of her mother, whom she has lived with for her whole life. At the funeral, her brother Todd and his wife Cynthia try to persuade her to sell the house, especially the possessions, as she is a hoarder. Her only close friend is the fiery Roz, though she also gets along with Roz's granddaughter Vivian. On her way to work, where she has been doing data entry for decades, she meets new young co-worker John, with whom she is immediately infatuated. Empowered by self-improvement tapes, Doris decides to go after him..

Plot Keywords: older woman, young man, co-worker, single woman, granddaughter, best friend, amusing ...

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#7. Love in Another Town (1997)

Storyline: The Capomezzo's and the Malacici's are Italian-American families who are also rivals in the catering and restaurant business. Things come to a head when the Capomezzo's son and the Malacici's daughter get thrown together for the leads in a Romeo & Juliet community play. As the parents continue butting heads, the children fall in love and hilarity ensues.—mahajanssen

Plot Keywords: divorcée, older woman, young man, love interest, lover, cougar, engaging ...

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#8. A Teacher (2013)

Storyline: Diana Watts is an English teacher at Westerbrook High School in Austin, Texas. A longtime and continuing undisclosed issue between her and her mother may be only one factor in Diana looking for love in the wrong place. That place is at school, as she has just embarked on a secret affair with one of her students, Eric Tull. This relationship is the most fulfilling she's had in quite some time. A few incidents and the first real close call in being caught leads to Diana calling off the affair several months in, as she finally comes to the understanding that being caught would certainly mean the end of her teaching career and her good reputation. This close time away from Eric also gives Diana the opportunity to look at their relationship through a slightly different perspective, with the old adage of absence making the heart grow fonder kicking in. As such, Diana gets torn between doing what she knows is the right thing by staying away from Eric, or listening to her troubled heart, her growing obsession and need for what she considers love which may make staying away from Eric difficult.—Huggo

Plot Keywords: english teacher, young woman, mother, student, moving, intense, confident ...

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