25 Best Older Woman Younger Man Romance Movies

Older woman-younger man relationship movies are a rarity everywhere. One wonders why. We already know that “way too older men-younger women” romance in movies is common. Today, we have decided to dig out movies where a woman romances a younger man. Such relationships typically give rise to fascinating scenarios. And that’s why these movies are so interesting to watch. For some people, these movies might be an uncomfortable experience. But most are going to love them for their intricate portrayal of complicated relationships. The following movies present this dynamic in the most interesting ways.

25. The Lifeguard (2013)

‘The Lifeguard’ is the tale of a disillusioned woman who has seemingly lost it all in her career and started working at a menial job. The narrative of Leigh, the said journalist turned lifeguard, takes a sharp turn when she falls in love with a much younger teenage boy, Little Jason, who is the son of the maintenance man. What starts as an acquaintance gets blown up into a full-fledged affair with frequent indulgences in sexual encounters. Another twist in the tale occurs when one of their mutual friends commits suicide, citing depression and withdrawal. The steamy affair of Leigh and Little Jason comes to an abrupt end, with both of them realizing some things aren’t meant to be. You can watch the movie here.

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24. How Stella Got Her Groove Back (1998)

Directed by Kevin Rodney Sullivan and starring Angela Bassett, Taye Diggs, Whoopi Goldberg, and Regina King, ‘How Stella Got Her Groove Back’ centers on 40-year-old successful stockbroker/single parent Stella. Responsibilities abound with no luck in romance, she is advised by her best friend, Delilah Abraham, to take a vacation to Jamaica. There, Stella gets romantically involved with 20-year-old Winston Shakespeare. Now, she has to decide if and how she is going to manage her long-distance love life, her professional career, and her motherhood. How she does it is what the movie entails. You can stream it right here.

23. I Could Never Be Your Woman (2007)

Directed by Amy Heckerling, ‘I Could Never Be Your Woman’ stars Michelle Pfeiffer, Paul Rudd, Saoirse Ronan, and Tracey Ullman. In the movie, we get to see Mother Nature pulling the necessary strings to bring 40-year-old divorced mother/producer Rosie face to face with 29-year-old actor Adam. As they begin dating, complications arise from their age gap. With Pfeiffer and Rudd looking perfect and doing full justice to their respective roles, ‘I Could Never Be Your Woman’ is a true-to-form romantic comedy that is a must-watch. You can do so right here.

22. The Proposal (2009)

Directed by Anne Fletcher, ‘The Proposal’ is a rom-com that is considered one of the best in the genre. Starring Sandra Bullock and Ryan Reynolds in the leads, the movie tells the story of Margaret Tate, a Canadian native, who is the editor-in-chief at a publishing house in New York City. When she faces deportation due to the violation of visa terms, she decides to marry her assistant, Andrew Paxton, an American citizen, as it will get her a green card. With an immigration officer stalking them, the two need to be careful about every step they take, and this results in hilarious situations. To find out whether Margaret gets her visa, you can stream the movie here.

21. The Age of Adaline (2015)

Directed by Lee Toland Krieger, ‘The Age of Adaline’ is a romance that tells the story of Adaline Bowman (Blake Lively), who has remained 29 for eight decades after being struck by lightning in 1937. While she has been continuously changing her identity and living a solitary life to keep her secret, an encounter with charming Ellis Jones (Michiel Huisman) makes her want to spend her life with him. But is love, romance, and growing old together possible for someone who is immortal? To know if Adaline gets what she wants, you can watch the film here.

20. What Every Frenchwoman Wants (1986)

Also known as ‘Exploits of A Young Don Juan,’ this movie is a French-Italian coproduction that relates the sexual awakening of a 16-year-old teenager and his various adventures within it. After being unsuccessful in this category, Roger finds plenty of women with whom to find pleasure after World War I breaks out, and men are suddenly nowhere in sight. However, his erotic experiences have consequences when not only the maid but other women he has slept with become pregnant from his exploits. Opposite to the tragedies of “Malèna” and the platonic interactions of Renato, this movie is a light, fresh, and at times comedic, well-shot picture of a young teenager’s exhilarating hormones.

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19. Adore (2013)

Perhaps one of the weirdest of them all, ‘Adore’ has a very experimental storyline comprising two older women and their sons, and incidentally, the women fall for each others’ sons. Marginally incestuous, the narrative further explores their “relationships,” which are nothing but hanging by a thread, and the after-effects of their short-lived affair. As open-ended as the movie was at the conclusion, this guilt-free tale of two mothers and childhood friends, Roz and Lil, and their never-ending adoration for their mutual sons (even after the latter are married and have kids of their own) is unforgettable, to begin with, and was both praised and panned in various circles. Naomi Watts and Robin Wright are at their sultry best, and their bolder demeanor isn’t worth a miss. Feel free to check out the movie here.

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18. Young Adam (2003)

As open and unrelenting as the title is, ‘Young Adam’ is the story of a drifter, Joe (Ewan McGregor), who is shown having sex with multiple women across multiple timelines in the movie, most notably with the wife of his boss Ella (Tilda Swinton). As Joe works his way out of his mundane life at the barge on the Clyde River, his deepening relationship with Ella, his past with Cathie, whose dead body has recently been pulled out of the river, of which Joe knows a lot more than he shows and his one-off physical relationship with Gwen, Ella’s sister, he becomes more and more embroiled in the past and present. Eventually, we get to see a different kind of courtroom drama as the movie heads toward its conclusion. Watch it only for McGregor’s performance and the everlasting sex.

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17. Don Jon (2013)

Written and directed by Joseph Gordon-Levitt, ‘Don Jon’ is a rom-com starring Levitt alongside Scarlett Johansson, Julianne Moore, and Brie Larson. The story revolves around New Jersey bartender Jon Martello who is a porn addict that has barred him from getting romantically involved with a woman. However, he doesn’t complain about it at all and is rather satisfied and happy with his active sex life and pornography. However, when he meets Barbara Sugarman and tries to get in bed with her, he realizes that she expects more and that he is ready for it too. What follows is how Jon courts her, disregarding all that he thought he needed and taking a new path. Will he be successful in it? To find out, you can check out the film here.

 16. Unfaithful (2002)

Arguably one of the biggest flicks of Diane Lane’s career, which became infamous for the nudity and sex (with a younger man), ‘Unfaithful’ as the name suggests, is the story of a married woman with a young bookseller, an affliction which soon gets blown out of proportions. A tale of nascent love transforming into uncontrollable lust, the story begins with Edward and Connie, who, along with their eight-year-old son Charlie, are leading an idyllic life in NYC. Connie bumps into a handsome young lad, Paul, who seemingly sweeps her off with his charm. As the plot thickens and as Paul and Connie start dating unbeknownst to Edward, things take an ugly turn when the latter begins doubting his wife’s loyalty. Anger and rage come in many forms, as is evident at the end of the movie. ‘Unfaithful’ is arguably one of the finest thrillers on this list. You can watch ‘Unfaithful’ here.

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15. Water for Elephants (2011)

One of the underrated movies featuring Robert Pattinson in a leading role, ‘Water for Elephants’ is the story of a young lad Jacob who has lost his parents and is left without a job. Given his skills as a veterinarian and his desperation for work, he finds a job as a vet at a circus, which is run by August, the ringmaster and animal trainer. Jacob gets smitten by August’s wife, Marlena and there begins a love story in the backdrop of circus cruelties and the atrocities on the circus workers. More often than not, ‘Water for Elephants’ has been rated high on freshness and a story that is rather unheard of, if you could ignore the shallow characterizations and weak performances. You may watch it here.

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14. The Mother (2003)

The movie begins with an elderly couple, Toots and May, who have grown to be increasingly dependent on each other. As they’re visiting their children and grandchildren, Toots dies of illness, and May remains aloof with her strenuous relationships with her children – most notably her daughter Paula, who is seeing a young man named Darren, the best friend of Bobby, May’s son. Incidentally, Darren is also married, which raises May’s concerns over Paula seeing him. As things turn out, May and Darren begin a sexual relationship, and suddenly, everyone is caught between a rock and a hard place. While not the best of “Older Woman Younger Man” movies so far, yet, this eyebrow-raising movie is famous for its performances and its unique premise.

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13. All Things Fair (1995)

A Swedish film set in the era of WWII, ‘All Things Fair’ is also the last film by Bo Widerberg and is set in the south of Sweden, where a story of controversial love and sexual desires takes place between a female teacher and her student. Stig is a 15-year-old student who is exploring his sexuality when he deeply falls under the charm of his teacher Viola’s attractive maturity. Viola, being more than twice his age, enjoys his youth as an alleviation of her alcoholic husband, and they soon start a sexual relationship. However, things aren’t easy for this unusual relationship, and one way or another, it will find its abrupt, unwelcoming end. In all fairness, ‘All Things Fair’ is a genuine effort and the story of a boy rooting and falling for his teacher received many awards and accolades, most notably the nomination for the Academy Award for Best Foreign Language Film. You can stream the film here.


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12. I Am Love (2009)

An Italian film at the outset, ‘I Am Love,’ revolves around the narrative of the Recchi family, a textile manufacturing giant based in Milan. Emma is the wife of Tancredi Recchi, the wealthy magnate who is to inherit his paternal wealth from his predecessors. Emma stumbles upon Antonio, a chef who is the best friend of Eduardo, Emma’s son. Soon, Emma finds her way to meet Antonio while they increasingly slip away into an intimate, physical relationship. Yet another Tilda Swinton movie on this list, wherein Swinton has essentially portrayed the older woman, ‘I Am Love’ is a cutting-edge melodrama, and Swinton, as usual, has won us all over with her performance. Called as “fascinating” and “timeless” by many, ‘I Am Love’ is like a breath of fresh air. You can stream it here.

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11. 5 To 7 (2014)

Featuring the late Anton Yelchin and Berenice Marlohe in leading roles, ‘5 to 7’ revolves around a struggling young writer, Brian, who lives in NYC and who meets up with a French middle-aged lady, Arielle, who has been married to a diplomat named Valery with two kids. In a strange turn of events, as Brian and Arielle begin a passionate (yet extramarital) affair, Arielle reveals that every day between 5 and 7 in the evening, she and her husband are, owing to an agreement, allowed to have an affair with anyone, if the affair confines within these time limits. Valery too, on the other hand, is in a relationship with a girl named Jane. As both Brian and Arielle progress in their relationship, Brian proposes and gives Arielle a ring to commemorate their so-called affair. The movie garnered accolades for performances, direction, and a watertight screenplay despite having a cliched rom-com kind of storyline. You can stream it here.

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10. Summer of ’42 (1971)

As is evident from the posters or the trailers, clearly, ‘Summer of ’42’ is one of the boldest “Older Woman Younger Man” movies to date. Mind you, it was released in 1971 when such a relationship could’ve been more stigmatized than what it is today. ‘Summer of ’42’ follows a rather simplistic storyline -during the summer of 1942, three pubescent teenagers, Hermie, Oscy, and Benjie, are leading an idyllic life, far from the commotion of the Second World War. Enter Dorothy, the wife of an army pilot whose husband is on the war front.

Although Hermie is the emotional chap from his group, he approaches Dorothy, and both form a symbiotic relationship wherein Dorothy meets Hermie in exchange for small chores. Notwithstanding their expectations, the relationship grows out of proportion, something even Hermie and his friends, who actively wanted to explore their sexualities but not to the extent of sex, couldn’t have imagined in the wildest of their dreams. Widely considered one of the most successful movies to date, the movie also went on to win an Academy Award for the best background score. You can check out the movie here.

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9. Notes on a Scandal (2006)

A disturbing little film about a school teacher, Barbara, who falls for one of her teenage students, Sheba, ‘Notes on a Scandal’ is, apart from its presentation style, nothing we haven’t seen in umpteen movies and television series. Soon, both start having a passionate affair. But things get complex when Barbara comes to know about Sheba’s affair with another teenage student named Steven. Given Barbara’s inhibitions on their affair and given Sheba’s stubbornness in maintaining both sides of her relationship, ‘Notes on a Scandal’ is a performance-intensive complicated affair in which nobody wins until the end. Blanchett is superb as the vulnerable teacher, knowing what she is doing is wrong, but then is stunned at the level of treachery the older woman, brilliantly played by Judi Dench who lashes out at her. It is a sensual film, but it is also downright frightening at times. You can watch the film here.

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8. Malena (2000)

This Italian drama is about a 12-year-old boy, Renato getting infatuated by the beauty of a sensual woman named Malena. Amidst the ongoing war, he discovers himself and, at the same time, helplessly sees the world around Malena crumbling apart due to the small-mindedness of the people in the town. As he begins to stalk her and steal her things, Malena’s world comes closer to the teenager Renato, followed by some marginally disturbing sex scenes. Critics had lashed out at the film when it was released, but since then, it has garnered a cult following, and deservedly so. It may not be the most subtle film, but it certainly is a beautiful and sad take on one-sided love. You may watch the film here.

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7. The Piano Teacher (2001)

It’s impossible to pin down a Michael Haneke film for such a short write-up. So, let’s just get straight to the point. ‘The Piano Teacher’ explores a disturbing sexual relationship between a middle-aged piano teacher, Erika, and one of her handsome young students – Walter. Erika’s mother controls her sexual life, and this has turned her into a shattered soul with sadomasochistic fantasies, including self-mutilation. Her tumultuous relationship with Walter changes radically, and he becomes disgusted with her, thus abusing and assaulting her. This shatters Erika, and she throws herself into the darkest abysses of human existence. ‘The Piano Teacher’ is a film that will disturb, devastate, and move you in ways you haven’t been before. Feel free to check it out here.

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6. The Reader (2008)

‘The Reader’ tells the story of a boy Michael who develops a sexual relationship with an older woman Hanna in the backdrop of impending trials seeking answers on the Nazi concentration camps. They first meet when the boy feels sick while traveling in a tram and later meet up in her apartment, where she seduces him and they make love. They begin to see each other more frequently in her apartment, and she insists he reads literary works he’s studying after they make love every time. However, her past comes back to haunt her, and this wrecks their relationship, leaving a lasting impact on the two.

‘The Reader’ is set in two different timelines and is a gorgeously flawed masterpiece that beautifully depicts an enigmatic relationship between a teenager and an older woman and years later when they meet and confront each other in the courtroom. Kate Winslet gives a performance of her lifetime and has deservedly been bestowed with an Academy Award for Best Actress in a Leading Role for her performance in the movie. You can check out the film here.

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5. Y Tu Mama También (2001)

From director Alfonso Cuarón, this film greatly depicts the sexual desires and discoveries of the typical teenage youth through a film that offers more than what it shows at first glance. Julio and Tenoch are two friends living in Mexico whose girlfriends are leaving for a holiday overseas. After meeting the wife of a cousin of Tenoch, they convince her to join them on a road trip through the country after she discovers about her husband’s infidelity. On this voyage, sex and friendship will be key elements that will endure discoveries, changes, and self-reflection. ‘Y Tu Mama Tambien’ is oftentimes fearless and brutal, without fearing the preconceived sexual notions or the taboos associated with it. It is not every day that we get to witness a movie from the kitty of Alfonso Cuaron – a towering adventure you cannot forget. You can watch ‘Y Tu Mama También’ here.

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4. Rushmore (1998)

Touted as a love story at the outset, ‘Rushmore’ derives its name from the Rushmore Academy, a private school where Max and Blume, the best buddies, are studying. Incidentally, both fall for their widowed schoolteacher, Rosemary and leave no stone unturned, unbeknownst to each other, that they can do to woo Rosemary. As things unfold and Max and Blume turn against each other to win over Rosemary, Max eventually has to give up owing to his emotional turmoils. All is well that ends well is a quote aptly justified in this movie. ‘Rushmore’ caused a massive cult following with relatable characters and exceedingly good performances. You may watch it here.

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3. Harold and Maude (1971)

‘Harold and Maude’ has an almost creepy, morbid storyline. An 18-year-old Harold, who is obsessed with death, meets an optimistic 79-year-old lady, Maude, and they develop a romantic relationship. The awkward tone the film maintains throughout is quite fascinating, and the way it depicts such a strange and unusual relationship with such warmth, humor, and humanity is simply astounding. The film did not sit well with audiences and critics back when it was released in 1971 for very obvious reasons, but it has managed to attain a strong cult following among cinephiles, and after frequent revisits and revaluation, critics have considered the film to be one of the funniest films ever made. You may watch ‘Harold and Maude’ here.

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2. The Graduate (1967)

The one entry, I assume, that wouldn’t surprise our readers. ‘The Graduate’ defined romance and sexuality for a generation, and it continues to resonate in the way it captures the madness, frailties, and excitement of youth. ‘The Graduate’ tells the story of a 21-year-old Benjamin Braddock, with no aim in life, who is seduced by the wife of his father’s business partner. They develop an unlikely relationship, but things take an ugly turn when the ever-confused Benjamin falls in love with her daughter. The film is a funny, honest depiction of youth, romance, and the inherent uncertainties of human relationships and destiny. It’s sad, hilarious, and also beautifully emotional. You can stream the film here.

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1. A Short Film About Love (1988)

‘A Short Film About Love’ is a film that has grown on me tremendously with time. The way Kieslowski manages to portray the sheer tenderness of love here is simply beyond words. The film explores the relationship between a teenage boy and an older promiscuous woman whom he spies on from his window. She does not believe in love and is way beyond the naivety of a teenager who thinks he’s in love but is only infatuated with her. She dismisses his feelings but later begins to see his love. The ‘Dekalog’ version of the film has a slightly better ending, in my opinion, with the boy realizing that it was not the love that was between them but more of a mere sexual fantasy. This was far more powerful and tragic than the more fairytale-ish ending of the movie. Additionally, it remains one of the greatest romantic films ever made.

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