16 Great Romance Movies Where An Older Woman Dates A Younger Man

While an age gap romance with an older man is seen as more common, there are plenty of great movies about an older woman dating a younger man. These movies are sometimes difficult to pull off without falling into cliché, and the idea of too big of an age gap can be offputting. However, this is not always the case, and some films treat these romances with the respect they deserve. Love can look like many things, whether a friendship, a family bond, or even a relationship that strays from the usual conventions of “acceptable” love.

Many of these films center the age difference in the plot, even in movies like The Graduate, where the actors playing them are closer in age than their characters. However, sadly, in some movies that showcase a romance where there is a significant age gap between the two leads, viewers can be met with a story that seeks to sexualize and fetishize the age difference, with the “MILF” storyline in American Pie as a good example. However, some movies create a lovely onscreen representation of love between an older woman and a younger man.

16 Lonely Planet (2024)

A Struggling Writer Begins An Affair With A Younger Man At A Morrocan Retreat

Lonely Planet is the latest movie to explore the dynamic between an older woman and a younger man. The Netflix drama stars Laura Dern as Katherine, a writer who leaves behind her troubled life at home to visit a writer’s retreat in Morocco. Also at the retreat, accompanying his girlfriend, is Owen (Liam Hemsworth). With the two lonely souls quickly forming a connection, their friendship builds into an intense love affair.

Lonely Planet‘s age gap is considerable, but the romance between the two adults is not seen as scandalous because of their age difference but rather their own complicated love lives. However, the movie explores loneliness and the isolated feeling of being in a new place only to become tethered to someone new, similar to the relationship explored in another age-gap movie, Lost in Translation. It makes for a steamy and engrossing romance with a particularly great performance from Dern.

15 A Family Affair (2024)

A Famous Movie Star Begins Dating His Assisstant’s Mother

As some audiences can get unsettled by age-gap romances, it is not often that the subject is used for a comedy. However, A Family Affair found there was enough room for laughs along with the romance by addressing some of the awkwardness of it all. The Netflix comedy stars Joey King as Zara, the long-suffering assistant to a pompous movie star, Chris Cole (Zac Efron). The relationship is only made worse by the fact that Zara discovers that her mother, Brooke (Nicole Kidman), is having an affair with Chris.

The comedy is elevated thanks to the great chemistry between Efron and Kidman…

The sitcom-like premise goes for the laughs in how frustrated and mortified Zara is with this relationship. However, at the center of it all is a genuinely tough romance between Chris and Brooke. She helps him to be a better person and they struggle with Zara not accepting that they love each other. The comedy is elevated thanks to the great chemistry between Efron and Kidman, who bring out the comedy and the heart in the relationship.

14 Something’s Gotta Give (2003)

A Woman Is Torn Between A Man Her Age And A Young Doctor

Rom-com legend Nancy Meyers explored the subject of age differences in romances with Something’s Gotta Give. Jack Nicholson stars as Harry, a serial bachelor who enjoys dating younger women. However, after an embarrassing encounter, Harry finds himself drawn to one of his young girlfriends’ mothers, Erica (Diane Keaton), which changes his view of women and how he has approached his love life.

As Harry dates younger women, the more reserved Erica finds herself pursued by younger doctor Julian (Keanu Reeves), much to Harry’s annoyance. While the movie ultimately wants the audience to root for Harry and Erica to get together, it perhaps makes the mistake of presenting Erica and Julian as the more engaging couple. Keaton and Reeves have such wonderful chemistry that the movie’s message about two people finding love with each other later in life is somewhat undone.

However, the film is a funny and charming rom-com with an all-star cast of legendary actors. Keaton is especially good in the movie, scoring a rare Oscar nomination for a rom-com role.

13 Y Tu Mamá También (2001)

Two Teens Go On A Road Trip With An Older Woman

Oscar-winning director Alfonso Cuarón delivered one of his best projects with the coming-of-age movie Y tu mamá también which also takes one of the more interesting approaches to an age-gap romance. The Mexican film stars Diego Luna as Tenoch and Gael García Bernal as Julio, two teenage best friends who take a road trip with a woman in her late 20s, Luisa (Maribel Verdú). The trio bonds on this adventure together while the two boys harbor an infatuation with Luisa.

While they both pursue her separately, the climax of the movie features the iconic and sexy scene of the three of them surrendering to the passion together.

While the age gap is not as wide as in other movies, the relationships at the center of the story are engrossing. It is as much about the friendship between these two boys as it is about the affair they have with this older woman. While they both pursue her separately, the climax of the movie features the iconic and sexy scene of the three of them surrendering to the passion together. The movie is a beautiful and captivating experience that earned an Oscar nomination for Best Original Screenplay​​​​​.

12 Good Luck To You, Leo Grande (2022)

A Widower Hires A Sex Worker

One of the biggest age gaps in any rom-com comes in the intimate Good Luck to You, Leo Grande, which is more about connection than romance and sex. The movie stars Emma Thompson as Susan, an older woman who, following the death of her husband, addresses her life-long unhappiness with her sex life and hires a sex worker named Leo Grande (Daryl McCormack). The movie is told through several sessions these two strangers have with each other as Susan explores her sexuality and gets to know Leo.

There is an attraction between the two and a connection beyond the physical, but it is interesting that the movie never explores the idea of a romance between these two. They are both under the understanding that this is a transaction relationship, but that doesn’t stop them from enjoying each other’s company, blurring the professional lines. It is a simple yet entertaining movie that celebrates beauty and sexuality at older ages. Thompson earned a Golden Globe nomination for her performance.

11 How Stella Got Her Groove Back (1998)

A Middle-Aged Woman Finds Happiness On Vacation With A Younger Man

Released in 1998, Angela Bassett stars in How Stella Got Her Groove Back, a romantic comedy-drama based on the novel by Terry McMillan. The story has Bassett starring as Stella Payne, a 40-year-old single parent raising her son.

She always has to answer to her friends and family for being out of a relationship for too long. This situation changes when she vacations to Jamaica and meets Winston Shakespeare (Taye Diggs). Winston is 20 years younger than Stella, a chef’s assistant who falls in love with the woman. It is through their love that Stella finally finds herself.

The idea of the older woman dating a younger man in this movie is Stella finding happiness outside work and breaking out of her midlife crisis by finding her youth again with Winston. Angela Bassett stole the show, and won an NAACP Award for her performance.

10 Bull Durham (1988)

An Love Triangle Between An Older Woman, Her Young Lover, And His Older Coach

The central love story in Bull Durham is actually about two people around the same age, but an age gap is central to the story. Crash Davis (Kevin Costner) is a 12-year veteran sent down to the minor leagues to work with a hot-shot young pitcher. While working with the rookie, Ebby (Tim Robbins), both men end up falling for Annie (Susan Sarandon), an older woman who is a self-confessed baseball groupie, who picks a young player each year to have a fling with and teaches him all about sex, love, and life.

There are definitely problematic elements to the main plot, as the entire purpose of the older woman and younger man relationship here was that Annie always set out to seduce younger men every baseball season, as she felt it would improve their lives and gameplay. Despite this, it is a charming (if dated) film. However, it’s worth noting that in real life, the actors were all around the same age, and ironically, Robbins and Sarandon ended up getting married in real life.

9 Film Stars Don’t Die In Liverpool (2017)

A Real-Life Romance With A 29-year Age Gap

The story of Peter Turner and Hollywood film star Gloria Grahame is both heartbreaking and wholesome.Film Stars Don’t Die In Liverpool showcases the true history of their love story through memories, through ups and downs, and with a focus on the tragedy of her battle with cancer, and how it impacted their relationship.

The romantic drama creates a lovely onscreen portrayal of a true romance that very much took “Till Death Do Us Part” seriously.

The romantic drama creates a lovely onscreen portrayal of a true romance that very much took “Till Death Do Us Part” seriously. Film Stars Don’t Die In Liverpool may be tragically sad, but it shows romance’s ups and downs and pays little attention to the obvious age gap.

The real-life age difference was 29 years, with Turner 27 years old when they started dating and Grahame was 55 at the time. She died two years into their relationship at 57. Bening won the AARP Movies for Grownups Award for the film, and Bell won the New Hollywood Award.

8 White Palace (1990)

An Unexpected Romance Between A Young Widower And A Middle-Aged Waitress

At first, White Palace looks like it will be another stereotypical addition to the age-gap romance genre – as a younger man falls for an older woman of a lower social class. In some ways, it would be easy to expect a Pygmalion story packed with cliches, but the film surprises its viewers and creates an endearing love story instead.

White Palace buys into the ‘instant connection’ trope when Max (James Spader) first meets Nora (Susan Sarandon), but the couple struggle with issues of public opinion, shame, and secrecy because of their age difference.

White Palace creates a conversation that strays away from the stereotype that renders older characters uninterested in sex while avoiding the seedy older woman/younger man complex. It helps that the age gap isn’t huge, as the characters are 27 and 43. The central theme is Max’s initial embarrassment at dating an older woman, hiding it from his friends and family, but eventually, he realizes the error of his thinking.

7 The Graduate (1967)

A 21-Year-Old Is Seduced By An Older Woman

The Graduate is a film with an iconic ending andone of the most famous love triangles in movies, making it a must-watch, despite some of the more problematic elements. The Graduate stars Dustin Hoffman as Benjamin, a young man fresh out of college, who doesn’t know what to do with his life.

He finds himself caught in a love triangle between Mrs Robinson (Anne Bancroft) and her daughter, Elaine (Katharine Ross) – with Mrs Robinson originally seducing the young man, and then Benjamin and Elaine falling for each other. The themes of power, control, and uncertainty loom large, with this being a film where the age-gap relationship definitely does not get a happily ever after.

It was controversial when it came out because of the relationship between the older woman and the younger man. However, Dustin Hoffman was 30 and only six years younger than Anne Bancroft at the time, although he played a 21-year-old college graduate. The movie earned seven Oscar nominations, winning for Best Director (Mike Nichols). The AFI calls it the 17th-best American movie of all time.

6 Don Jon (2013)

A Young Man Struggles To Find Real Intimacy Until He Meets An Older Woman

On the surface, Don Jon looks like a straightforward romantic comedy. However, it is much more than that, especially in its representation of Esther (Julianne Moore) and Jon (Joseph Gordon-Levitt). Esther and Jon meet at community college, and despite Jon’s existing relationship with Barbara (Scarlett Johansson), they end up finding something real together.

Esther and Don Jon represent one of the most open and honest portrayals of mutual understanding, and they also have a great sexual bond. Their relationship showcases a healthy portrayal of love through non-judgment, with each character developing throughout their relationship. The movie is also a commentary on intimacy, cheating, and control, as Jon struggles to connect with women his age, and it isn’t until he finds an older woman that he learns how to be vulnerable.

Before Esther, Jon mostly has a casual sex life but finds more satisfaction with pornography, which costs him relationships with younger women (including Barbara). However, with Esther, the age gap removes much of the expectations, and they can freely lose themselves when becoming intimate, finally fulfilling their needs.

5 The Age Of Adaline (2015)

An Ageless Woman Falls For A Younger Man

The Age Of Adaline is a fantasy romance movie that tugs on the heartstrings, as a woman who cannot age falls for a young man, knowing that they cannot grow old together. Adaline (Blake Lively) and Ellis (Michiel Huisman) may look the same age, but Adaline was over 100 years old when they meet and fall in love. Unfortunately, his father was a previous love of hers and may reveal her secret.

This is a sweet, complex story of magical realism and one that often doesn’t feel like an age-gap romance because the leads appear to be the same age. This is not the only film that uses fantasy to create an age gap that doesn’t feel like an age gap, either.

While some of these films show an age gap this big that is problematic (such as vampire movies like Twilight, where an immortal connects with a teenager), in this case, Ellis is at least in his 30s – so while the age gap is decades, it is between adults. In addition, Adaline was trapped in her never-aging body and deserved her eventual happy ending.

4 I Could Never Be Your Woman (2007)

A Refreshing Rom-Com About An Age-Gap Couple

I Could Never Be Your Woman is a romantic comedy about an older woman who is a writer and a producer, and the younger actor who she casts in her show. Adam (Paul Rudd), refreshingly, doesn’t care what others think about him, or their relationship. This forces Rosie (Michelle Pfeiffer) to think of their relationship differently – and despite the usual rom-com roadblocks and misunderstandings, their happy ending feels real.

The movie removes the restraints age puts on love and makes for a wholesome, heartwarming, and hilarious watch.

The age gap between the characters is also only 11 years, but seeing a 49-year-old divorced woman find love with a younger man who doesn’t care about the difference is refreshing. The movie removes the restraints age puts on love and makes for a wholesome, heartwarming, and hilarious watch.

The rom-com has the typical tropes, with misunderstandings and people working against them, but the age gap is only a small part of what gets in the way of love. While it ended up going straight to DVD, it received mostly positive reviews, with credit going to the positive representation of a relationship despite the characters’ age differences.

3 The Proposal (2009)

A Fake-Dating Rom-Com With An Implied Age Gap

The Proposal employs the fake dating trope alongside hilarious scenes between Andrew (Ryan Reynolds) and Margaret (Sandra Bullock). While the movie never made a huge deal about the age gap between them, Andrew was her PA (forced to pretend to be his boss’s fiance so that she can keep her work visa), so the story implied she was at least a fair number of years his senior.

The relationship between the two also emphasizes this subtly by Margaret being much more put together than Andrew. There are problematic moments, with Margaret using her power as Andrew’s boss to force him into pretending to be her boyfriend and putting him into uncomfortable situations, which is a clear abuse of power.

But in the end, the two fell in love anyway. Their onscreen chemistry was mirrored in their healthy relationship, which developed between them, earning them nominations for Best Couple at the People’s Choice Awards.

2 Harold And Maude (1971)

A Black Comedy And A Significant Age Gap Romance

Harold And Maude is a perfect example of a great romance between an older woman and a younger man from the moment the pair meet. Through acts of service and personal affection, the pair develop a complete love for one another despite the considerable age gap.

The couple highlights what a healthy relationship looks like. The movie is a black comedy, with Harold as a young man obsessed with death who falls in love with Maude, who is 79. Despite the 50 year age difference, Maude seems more upbeat and ready to keep enjoying life than the morose Harold, but when he starts to get to know her, he begins to really appreciate life for the first time.

Maude helps Harold move away from his somewhat boring life while Harold helps Maude to re-discover her youth. Ultimately, the movie ends in a tragedy, but the time the pair spent together left viewers with a new outlook on relationships with an age gap.

1 The Idea Of You (2024)

An Older Woman Falls For A Young Celebrity

The Idea Of You
was a huge hit when it launched on Prime in 2024, with the central age gap (and the age of star Anne Hathaway) sparking significant conversations.

The Idea Of You was a huge hit when it launched on Prime in 2024, with the central age gap (and the age of star Anne Hathaway) sparking significant conversations. The film follows divorcee Solene (Hathaway), as she accidentally meets boy band member Hayes Campbell (Nicholas Galitzine) when attending Coachella with her daughter.

The two have instant chemistry, but Solene is uncomfortable with the idea of a flirtation, because of their 16 year age difference, and her daughter’s past love of his band. Despite this, Hayes pursues her, and the two eventually start a romance. The film does an excellent job of exploring the ways that the age gap – and the issues of fame – impact this burgeoning relationship, and how it affects Solene’s work and family.

And, while a happy ending is guaranteed in a rom-com, it doesn’t come easily. And unlike many films with this kind of age gap, the element of celebrity goes a long way to balance the power dynamic. Although Solene is older and more experienced than Hayes, his stardom balances the scales, giving them a surprisingly healthy on-screen relationship that is easy to root for.