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For decades, there’s been a certain relationship trope in movies that we haven’t exactly been a fan of, and that’s men being romantically involved with younger women. Now, we’re not saying that all these films are bad movies — honestly, we’ll watch Humphrey Bogart and Lauren Bacall any day. But because these types of romances have been so normalized, we really don’t often see enough stories about the opposite: women who have relationships with younger men. And when we do, we talk about them like they’re anomalies or somehow taboo — think The Graduate or Daniel Craig-led The Mother, in which older women pursue their daughter’s romantic interests.
Now that’s not to say that we want all relationship with major age gaps to be normalized and some films do a great job of calling out dangerous age gaps between men and women. There is most definitely a line and just like with some romances between older men and younger women, plot lines with much younger men dating an older woman can be uncomfortable viewing. However, some movies manage to pull off displaying older women as desirable, sexual beings without glorifying power imbalances or inappropriate age gaps.
In recent years, we’ve seen a shift in some depictions of women who pursue, date, or have relationships with younger men, even if it’s hardly a cinematic mainstay. New additions to the genre like Something’s Gotta Give show that these dynamics don’t have to be any more complicated than when older men date younger women — which, as we’ve pointed out, happens so often in film that we’d struggle to round it down to a top 500.
From hidden gems like The Good Girl, starring 21-year-old Jake Gyllenhaal and 32-year-old celebrity crush Jennifer Aniston to the decidedly darker The Reader, starring Kate Winslet in her Oscar-winning performance, these movies all took a stab at showing the real-world Olivia Wilde-Harry Styles dynamic on-screen, for better or for worse. Read on to see which of your favorite actors have coupled up with slightly-to-much older ladies for a movie romance.
A version of this article was originally published on Oct 2021.
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‘May December’
Image Credit: ©Netflix/Courtesy Everett Collection Julianne Moore, Charles Melton and Natalie Portman star in May December which is getting a lot of buzz ahead of the 2024 award season.
The film is loosely based on the real-life story of Mary Kay Letourneau. In the Netflix movie, Moore plays a former teacher who groomed and started a relationship with her 13-year-old student.
Over two decades later, an actress (Portman) comes to spend time with Moore’s character and the now-adult student (Melton) as she preps to portray their romance on screen.
In an interview with Katie Couric, Moore said that the movie explore on her character’s desire to shape the narrative around her inappropriate relationship in order to victimize herself rather than admit her guilt.
“Everyone is so desperate to express their narrative, to tell their story — no one more so than Gracie. And Gracie’s narrative is so complicated,” she said.
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‘The Proposal’
Image Credit: Sam Emerson/©Walt Disney Studios Motion Pictures/Courtesy Everett Collection In The Proposal, Sandra Bullock plays a powerful executive editor-in-chief at a New York publishing company who faces deportation to Canada due to a visa term violation. She blackmails her assistant, played by Ryan Reynolds, into marrying her for a green card. While the circumstances of this movie might start out a bit less than ideal, the two find they really do have feelings for one another. What we really love about this film is that the age difference between the stars (Bullock is 12 years older than Reynolds) isn’t actually given too much attention. The focus here is solely on the budding romance rather than an older woman having a romantic relationship with a younger man.
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‘White Palace’
Image Credit: ©Universal/courtesy Everett Collection. Starring James Spader and Susan Sarandon, White Palace is a sexy, poignant look into this type of age gap dynamic. Sarandon plays a working-class woman, while Spader plays a more white-collar gentleman who finds a connection in their carnal desires.
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‘Don Jon’
Image Credit: ©Relativity Media/Courtesy Everett Collection Don Jon is all about a man named Jon who isn’t satisfied with the sexual encounters he faces, until meeting a fellow college classmate Esther who teaches him what he may think he wants isn’t exactly the right choice. This witty, poignant movie has grown a cult following for its honest portrayal of sex.
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‘The Dressmaker’
Image Credit: Everett Collection / Everett Collection ‘The Dressmaker’ stars Kate Winslet as a dressmaker who returns home to her rural Australian town to help her elderly mother. She strikes up a relationship with a much younger local man, Liam Hemsworth, and seeks revenge on those who wronged her.
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‘Good Luck to You, Leo Grande’
Image Credit: ©Searchlight Pictures /Courtesy Everett Collection Good Luck to You, Leo Grande stars Emma Thompson who plays a widow who hires a sex worker on a night of sex, adventure, and self-discovery.
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‘The Age Of Adaline’
Image Credit: ph: Diyah Pera/©Lionsgate/courtesy Everett Collection. The Age Of Adaline is a unique romance fantasy film starring Blake Lively as Adaline, who was struck by lightning, making her stay 29 years old physically forever. She has to stay on the run from the FBI, who wants to study her lack of aging. She falls for a man, whose father she knew decades earlier. This unique tale goes in-depth on their romance, a decades-spanning age difference between them.
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‘I Could Never Be Your Woman’
Image Credit: ©Weinstein Company/courtesy Everett Collection. Starring Michelle Pfeiffer and Paul Rudd, the 2007 comedy I Could Never Be Your Woman follows a mom falling for a younger man while her daughter falls in love for the first time as well.
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‘The Boy Next Door’
Image Credit: ©Universal/Courtesy Everett Collection Jennifer Lopez stars as a high school teacher who has a one-night stand with her 19-year-old student after her husband cheats on her. However, the student soon becomes dangerously obsessed with her.
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‘P.S.’
Image Credit: (c) Newmarket/courtesy Everett Collection. P.S. is about a divorced woman who starts a relationship with a young man who looks a lot like her deceased high school sweetheart.
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‘The Rebound’
Image Credit: ©Weinstein Company/courtesy Everett Collection. The Rebound follows a single mom who strikes up a relationship with her new, younger neighbor. Watch it on Peacock!
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‘Film Stars Don’t Die In Liverpool’
Image Credit: ©Sony Pictures/Everett Collection. Like Judy, Film Stars Don’t Die In Liverpool takes a look at another real-life star who had a relationship with a younger man. for the last two years of her life, Gloria Grahame (played by Annette Bening) was in a relationship with Peter Turner, who would go on to chronicle their romance and Grahame’s final days in his book, of which the film is based on.
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‘Judy’
Image Credit: David Hindley / © Roadside Attractions / courtesy Everett Collection. Based on the final chapter of Judy Garland’s life, Judy takes a closer look at her fifth and final marriage to Mickey Deans, who was roughly 12 years Garland’s junior. Renée Zellweger plays the legendary screen star in the film that earned her a second Acadmey Award, with Finn Wittrock as Mickey.
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‘The Graduate’
Image Credit: Courtesy Everett Collection. We decided to save what might’ve been the most obvious choice for this list for last. The Graduate is one of director Mike Nichols’ most iconic films, thanks in part to Anne Bancroft’s seductive performance as Mrs. Robinson. In the film, college graduate Ben Braddock finds himself torn between Mrs. Robinson and her daughter Elaine. It has a slew of memorable lines, moments, music and earn one Academy Award and six nominations.
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‘The Reader’
Image Credit: ©Weinstein Company/Courtesy Everett Collection. Kate Winslet’s turn in The Reader earned her an Oscar for her astonishing performance. The film, based on the novel of the same name, follows a teenager who has an affair with a woman only for one summer. After their relationship comes to a mysterious end, he recounts watching her defend herself on trial as a former guard for the Nazi party.
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‘Careful What You Wish For’
Image Credit: © Starz Digital Media /Courtesy Everett Collection In this thriller starring Nick Jonas, Isabel Lucas and Dermot Mulroney, a young man gets more than he bargained for when he begins a relationship with the wife of the investment banker who lives next door to his parents’ lake house. A suspicious death and a large life insurance policy soon cause him to be at the center of a scandal.
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‘Something’s Gotta Give’
Image Credit: ©Columbia Pictures/Courtesy Everett Collection. While Nancy Meyers’ beloved Something’s Gotta Give focuses on the burgeoning romance between Jack Nicholson’s Harry Sanborn and Diane Keaton’s Erica Barry, the relationship we absolutely adore from this movie is Erica’s romance with Keanu Reeves’ Dr. Julian Mercer. These two just bubble over with chemistry — no offense to Mr. Nicholson. And it’s just so refreshing to see an accomplished, self-assured character like Julian go after Erica! Get yourself a glass of white wine for this trip to The Hamptons and beyond!
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‘Adore’
Image Credit: Exclusive Releasing/Courtesy Everett Collection. Adore, starring Robin Wright and Naomi Watts, features two friends who go on a trip with their teenage sons. It’s a dramatic tale of betrayal and passion as the childhood friends fall for each other’s sons.
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‘The Good Girl’
Image Credit: ©Fox Searchlight/Courtesy Everett Collection Before Jennifer Aniston officially shed her Rachel Green image from Friends, the actress starred in this little romantic drama alongside a 21-year-old Jake Gyllenhaal. Justine Last (Aniston) is a store clerk who starts up an affair with a young man (Gyllenhaal) who fancies himself a real-life Holden Caulfield à la Catcher in the Rye. Their tryst only gets complicated as Justine tries to hide the affair from her husband Phil Last.
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‘Bull Durham’
Image Credit: ©Orion Pictures Corp/Courtesy Everett Collection. 1988’s Bull Durham features Susan Sarandon and her former real-life partner Tim Robbins along with Kevin Costner in this baseball movie romance. While the central love story might be between Costner and Sarandon, Robbins’ character is initially the one who catches the fancy of Sarandon’s character, Annie Savoy. Either way, though, Sarandon is actually older than both her leading men!
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‘How Stella Got Her Groove Back’
Image Credit: 20th Century Fox Licensing/Merch. If Angela Bassett is in a movie, you know we’re watching it. The Oscar-nominated actress is absolutely radiant in 1998’s How Stella Got Her Groove Back, and having Taye Diggs as her love interest isn’t that bad either! Bassett stars as Stella Payne, a career-driven single mom who seriously needs a vacation. On a trip to Jamaica with her friend Delilah (Whoopi Goldberg), she falls for Diggs’ Winston Shakespeare. What ensues is a sexy, fun, and flirty romp about a woman rediscovering who she is.
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‘The Mother’
Image Credit: Mary Evans/Ronald Grant/Everett Collection. Before he was James Bond, Daniel Craig started in a number of independent dramas, including The Mother. Craig stars alongside Anne Reid in a story about a woman who finds herself having an affair with the man who is sleeping with her daughter. Reid earned a BAFTA nomination for Best Performance by an Actress in a Leading Role for the film.
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