Movies With An Older Woman-Younger Man Romance

In Amy Schumer's "Last Fuckable Day" sketch, Sally Field is a punch line. She's the go-to example of how Hollywood marginalizes women of a certain age. Whereas male movie stars are consistently paired with love interests 10 or 20 years their junior (see: who's been cast opposite Tom Cruise in the new Mummy movie), Field was relegated to playing Mrs. Gump at the age of 47. Tom Hanks is merely 10 years younger than she is. Men get increasingly younger romantic partners; women have to play mothers.
But Field got the last laugh in Hello, My Name Is Doris, in which the actress pursues a man more than three decades her junior. Field plays Doris, who finds herself smitten with John Fremont (Max Greenfield), the new guy in her office. Bereft by the recent loss of her mother, for whom she cared her entire life, Doris passionately attempts to figure out how she could possibly win John. It turns out her zany wardrobe is a hit in Williamsburg, and the two end up becoming friends.
Doris may be a bit clueless, but the movie doesn't deny Field her sexuality. At one point, hipsters at a concert assume that John is sleeping with her. Sure, Doris is sort of dotty, and she certainly has no idea how to seduce a man, but she's still seen as desirable.
The history of movies featuring romantic and/or sexual relationships between older women and younger men is a fraught one. Yes, Mrs. Robinson is hot in The Graduate, but she's also portrayed as a boy-crazy lady who ruins lives. Cinematic women who engage in affairs with younger men are often sexy, but also broken in some way or another. Though the woman has the upper hand in terms of age, she is often a conquest for the virile dude.
Ahead, we look at some other movies featuring the age gap you're not used to seeing.
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Notes On A Scandal (2006)

Starring Judi Dench and Cate Blanchett, this psychological thriller exposes the darker side of such relationships. When art teacher Sheba Hart (Blanchett) arrives at St. George's, she forms a kinship with older teacher Barbra Covett (Dench). But when Barbra learns that Sheba's been having an affair with a student, all bets are off.
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Malèna (2000)

This isn't a romance so much as it is a movie about the obsession, and the way younger people often turn older people into symbols. Renato is 12 when he first sees Malèna (Monica Bellucci), a lonely woman waiting for her husband to return from the African front in WWII. Like the other people in his town, he's fascinated by her. For Renato, Malèna becomes a symbol for everything erotic, one that he can't shake throughout his life.
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The English Teacher (2013)

Raise your hand if you ever had a crush on your teacher. This one's for you. In this rom-com, Julianne Moore plays an English teacher in a small Pennsylvania town whose life is shook up when her favorite student from years ago, Jason (Michael Angarano), returns to town. They team up to produce one of Jason's plays. And then — wham, bam, feelings!
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Florence Foster Jenkins (2016)

You can spend the entire movie trying to figure out the relationship between Florence Foster Jenkins (Meryl Streep) and her devoted (and younger) husband, St. Clair Bayfield (Hugh Grant). St. Clair supports Florence as she pours her huge inheritance into her dreams of learning to sing, even though she has no talent. He clearly loves her, but also spends each evening with another woman, whom he loves too. The women know about each other. Florence and St. Clair's "arrangement" is fascinating to watch play out.
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Hello My Name is Doris (2015)

Doris' (Sally Field) sexual awakening takes place in an office elevator with her coworker, creative director John Fremont (Max Greenfield). This is the movie of a crush, and the extreme, endearing measures Doris takes to keep John in her life.
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Cheri (2009)

It's the turn of the century in France, and clearly mothers have a more...involved relationship with their sons' sexual maturing. A retired courtesan, Charlotte (Kathy Bates), enlists the help of her former colleague, Lea (Michelle Pfeiffer), in teaching her son the ways of the bedroom. But Charlotte never intended for Chéri (Rupert Friend) and Lea to fall in love, despite the 20 years that separate them.
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Don Jon (2013)

New Jersey native Jon (Joseph Gordon-Levitt) knows what's important in life: His family, the gym, and — of course — his porn-watching habits. His addiction to porn has rendered it impossible for Jon to have real relationships with women. All that changes when he meets two women: Barbara (Scarlett Johansson) and Esther (Julianne Moore).
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Being Julia (2004)

In the 1930s, Julia Lambert (Annette Bening), a famous stage actress, falls for a young American fan. Then, Julia discovers that Tom is using their torrid love affair to further his own acting ambitions. What's a masterful actress to do? Easy. She befriend's Tom's young girlfriend, and plots revenge.
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The Mother (2004)

Seeking something to revitalize her life, May, a depressed widow, finds herself in the arms Darren, a handsome handyman half her age. Darren (Daniel Craig) also happens to be married, and cheating on his wife with May's daughter. What a doozy!
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Sunset Boulevard (1950)
Norma Desmond (Gloria Swanson) is a terrifying vision of an older woman. She's a washed-up silent film star who ensnares a screenwriter (William Holden) and leads him to a fatal demise. Sunset Boulevard is a wonderful movie, but Norma both embodies and represents how Hollywood sees older women. Once past their prime, they are grotesque.
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The Graduate (1967)
No name is more synonymous with these relationships than Mrs. Robinson. Anne Bancroft is dead sexy as the iconic character who seduces Dustin Hoffman’s aimless Benjamin Braddock. But, like Norma before her, Mrs. Robinson also turns vicious as she tries to keep Benjamin from her daughter Elaine (Katharine Ross).
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Harold and Maude (1971)
The age gap gets even wider in Hal Ashby's classic. The bizarre tale is about the romance between a wild-child 79-year-old (Ruth Gordon) and a young man (Bud Cort) who stages suicides. They both like going to funerals. So much about this relationship could be off-putting, but it's ultimately sweet.
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Class (1983)
Jonathan (Andrew McCarthy) is an awkward prep school student. At a bar, he meets a gorgeous older woman, Ellen (Jacqueline Bisset), who surprisingly takes an interest in him. They start an affair, but it’s cut short when she realizes he lied about his age. They’ll meet again: Turns out, the woman is the mother of his BFF, Skip (Rob Lowe). Then the movie takes an icky turn. By its end, Ellen's checked herself into the hospital for psychiatric treatment, while Jonathan and Skip have had it out and made up. You see, bro friendship is more important than a woman’s mental health.
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Bull Durham (1988)
Susan Sarandon has two lovers in this baseball movie, in which she plays the older woman as hot sage. One is the more age-appropriate Kevin Costner, the world-weary minor-league catcher; the other is Tim Robbins, the upstart pitcher. (Robbins and Sarandon, who were married for more than 20 years, met on this film.)
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Thelma & Louise (1991)
Yes, Susan Sarandon’s in this one, too, but it’s Geena Davis’ Thelma who gets it on with a studly Brad Pitt in one of his very early roles. Thelma isn’t that much older than J.D., but her tryst with him shows her reclaiming her desires after she is sexually assaulted earlier in the movie. Unfortunately, J.D. turns out to be a grifter.
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How Stella Got Her Groove Back (1998)
Angela Bassett plays the workaholic Stella, a single mother. She takes a trip to Jamaica and gets hit on by Taye Diggs’ Winston Shakespeare. (That name! Those abs!) Stella is conflicted over his age and faces the judgment of her friends back home.
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American Pie (1999)
Ah, yes, Stifler’s mom. Jennifer Coolidge's horny American Pie creation sleeps with Eddie Kaye Thomas' Finch. She is purely an object of teen male fantasy.
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Y Tu Mamá También (2002)
In Alfonso Cuarón’s film, Luisa (Maribel Verdú) hooks up with not one, but two sex-crazed younger men (Diego Luna and Gael García Bernal). She goes on a road trip with them after finding out her husband has cheated on her. Throughout the entire trip, the audience ultimately learns, she's grappling with the notion that she's dying of cancer.
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The Good Girl (2002)
A mid-Friends Jennifer Aniston starred in this indie as Justine, a depressed 30-year-old retail clerk. Saddled with an unhappy marriage, Justine engages in an affair with new employee Holden (Jake Gyllenhaal). This is yet another example of the trope in which an older woman uses a younger man to revitalize her spirit. But tragedy is in the cards for these two.
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Tadpole (2002)
This Sundance hit features a mature-for-his-age 15-year-old who really wants to get with his stepmother (Sigourney Weaver), but first ends up with his stepmother's friend (Bebe Neuwirth). Basically, if a teenager is the type who name-drops Voltaire, middle-aged ladies will be all over him.
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Something’s Gotta Give (2003)
Nancy Meyers' rom com features both an older man-younger woman relationship and an older woman-younger man relationship. At the outset, Jack Nicholson romances Amanda Peet, who plays Diane Keaton’s daughter. Then Keanu Reeves romances Keaton. The movie, however, preaches that age-appropriate love interests are best: Keaton and Nicholson are the characters you want to be together — when you’re not ogling the gorgeous Hamptons interiors.
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The Reader (2008)
Kate Winslet won her Oscar for her role as Hanna Schmitz, who has an affair with a 15-year-old (David Kross) in the late 1950s. She asks her younger lover to read to her. But she has many secrets. She was a concentration camp guard and is illiterate.
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Adore (2013)
The plot of this movie is ridiculous enough to elicit giggles. Robin Wright and Naomi Watts are two smokin’ Australian moms, who each have an affair with the other’s equally smokin’ son.
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Nightcrawler (2014)
Typically, the older party is seen as a predator. Nightcrawler flips that switch. Jake Gyllenhaal’s exceedingly creepy Lou Bloom blackmails local news director Nina Romina (Rene Russo) into sleeping with him. In another movie, it would be Russo’s character sweet-talking Gyllenhaal’s, but Nightcrawler makes him the sinister, amoral leech.

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