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12 Great Romance Movies Where An Older Woman Dates A Younger Man, According To Reddit – TheFantasyTimes

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By Jitin Gambhir

12 Great Romance Movies Where An Older Woman Dates A Younger Man, According To Reddit

There are plenty of movies about romances between people of different ages, but when it comes to movies about women who love younger men, they are often rare and sometimes fail to deliver without falling into cliché tropes. However, this is not always the case and there are some films that treat these romances with respect and don’t shame the characters on either side of the love story. Love can look like many things whether that be a friendship, a family bond, or even a relationship that strays from the usual conventions seen of “acceptable” love.


When it comes to these movies, some love stories feature younger men and mature women, even in movies like The Graduate where the actors playing them are closer in age than the characters they portrayed. However, sadly, in some movies that showcase a romance where there is a large age gap between the two leads, viewers can be met with an ensemble of films that seek to sexualize and fetishize the age difference. In these cases, Reddit users recommended some movies that showcase this romance in a better light. These movies create some lovely onscreen representations of love between an older woman and a younger man.

12 How Stella Got Her Groove Back (1998)

Stella and Winston in How Stella Got Her Groove Back.
  • Streaming now on Prime Video

Released in 1998, Angela Bassett stars in How Stella Got Her Groove Backa romantic comedy-drama that is based on the novel of the same name. The story has Bassett starring as Stella Payne, a 40-year-old single parent raising her son. She has to answer to her friends and family for being out of a relationship for too long. This all changes when she takes a trip to Jamaica and meets Winston Shakespeare (Taye Diggs).

On Reddit, clothes recommended the movie, calling it “Prime.” 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 is finally able to find herself and for her and Winston, age was only a number.

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11 Bull Durham (1988)

Kevin Costner in Bull Durham

The main love story in Bull Durham is about two people around the same age. Crash Davis (Kevin Costner) is a 12-year veteran sent down to the minor leagues to work with a hot-shot young pitcher. That makes Crash in his early 30s, and he meets Annie, a baseball groupie who chooses one player to be her lover and student every season. Susan Sarandon played Annie, and she was 42 at the time.

However, the other love story was with the pitcher, Ebby. He was supposed to be a young rookie and Annie made him a man. Tim Robbins played Ebby, and he was actually 30 at the time. Stormy888 explained the plot, writing, “Susan Sarandon would “take one for the team” by “adopting” a ball player and play with him till he got good.” Ironically, Robbins and Sarandon ended up getting married in real life.

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

Gloria and Peter kissing in a pub
  • Rent now on Apple TV & Prime Video

The heartbreaking but wholesome story of Peter Turner and Hollywood film star Gloria Grahame is one to behold. Film Stars Don’t Die In Liverpool showcases the history of their love story through memories due to the return of her breast cancer. The romantic drama uses visual storytelling to create 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 is labeled by many fans including throwaway23er56uz as “a great movie, based on, or maybe only inspired by, the real-life of Gloria Grahame.” It showcased the ups and downs of romance and paid very little attention to the obvious age gap between the pair. This is what made it such a heartwarming watch with the couple’s families even being supportive of their infectious love for one another.

9 White Palace (1990)

Nora and Max share an intimate moment
  • Not available for streaming

At first, White Palace looks as though it is going to be another stereotypical sleazy addition to the age-gap romance movie. However, before it gets a chance to enter that world, the movie surprises its viewers and creates an endearing love story. White Palace sees a burst of chemistry when Max first meets Nora which soon leads to the couple being completely enamored with one another.

According to TheBigSalad84the movie is “a good one that not enough people have seen.” White Palace creates a conversation that strays away from the stereotype that renders older characters uninterested in sex, whilst avoiding the seedy older woman/younger man complex.

8 The Graduate (1967)

The Graduate iconic scene.
  • Streaming now on Prime Video & Criterion Channel

The Graduate contains one of the most complicated love triangles in history, making the movie such a compelling watch. The relationship between Ms. Robinson and Ben is something of a power dynamic where she holds all the power. Unfortunately, this plays into the stereotypes of a relationship with a large age gap. Whilst the movie does adhere to those tropes, it also provides an insight into the impact of age gaps.

Domslayer992 found the movie to be a “great examination of age gap relationships and how being in different stages in life could affect the relationship dynamic” by showcasing the conflicting lives of Ben and Ms. Robinson. The movie provides interesting dialogue regarding the couples working dynamic and contrasting lifestyles.

7 The Reader (2008)

Hanna Schmitz at her home looking down in The Reader

The Reader is a heart-wrenching story of love and betrayal that had fans hooked by its representation of the love between Hanna and Michael. It impacts the audience when Hanna ends up betraying Michael due to the investment in their story.

The love story between the two saw them act as role models to one another, with Hanna embracing life for what it is and Michael becoming more mature throughout their relationship. Reddit user inquirerman was as enamored with Kate Winslet as Hanna expressing how The Reader is a “wonderful Movie. Kate Winslet is mmmmmmm.” The movie also may not have the happy ending fans are after.

6 Man Of Steel (2013)

Henry Cavill Amy Adams in Man of Steel

Though there are many ways the makeup of the DCEU changed after the release of Man Of Steelthe movie proved to be a hit with fans, but even many ardent fans may have failed to recognize the hidden age gap between Lois Lane and Superman. Like every superhero movie, the hero protects the girl and their romance is an unconditional one. It undergoes so many challenges and setbacks but showcases that love always wins.

The relationship wasn’t so much about the onscreen ages, although some fans contested that Lois Lane is meant to be in her thirties. Clark, meanwhile, is just getting started in his career as Superman. Reddit user what_about_smee shared that they “doubt it’s meant to be noticeable.” The age gap adds another element of romance that acts as a welcome representation of love with an age gap.

5 Don Jon (2013)

Don Jon and Esther sitting by a fountain talking

Don Jon is a surprising movie that on the surface looks like a seedy romantic comedy. However, it is much more than that, especially in its representation of Esther and Don Jon. Esther and Don Jon represented one of the most open and honest portrayals of mutual understanding whilst also having a great sexual bond.

Their relationship showcased a healthy portrayal of love through non-judgment with each of the characters developing throughout their relationship. 22 grande 22 shared that “Don Jon is great,” especially in its representation of an older woman and younger man.

4 The Age Of Adaline (2015)

Adaline and Ellis meet in the elevator

The Age Of Adaline is one fantasy romance movie that played with viewers’ heartstrings. It was Adaline’s relationship with Ellis that won the hearts of fans. The pair may have looked the same age, but Adaline was over 100 years old when she fell desperately in love with Ellis. Unfortunately, his father was a previous love of hers.

The love between the pair was beautiful and something viewers would see in a Hollywood movie. Her love for Ellis is so strong that she broke her rule of dating, making it a heartwarming watch. Olivebranch99 shared that the movie “doesn’t get near enough recognition” especially for its romance that depicts an uplifting representation of love with an extremely large age gap.

3 I Could Never Be Your Woman (2007)

Rosie and Adam hugging in I Could Never Be Your Woman

I Could Never Be Your Woman may be a hilarious romantic comedy, but it also delves into the exact stereotypes that haunt older women who enter into a relationship with a younger man. Adam is one person that doesn’t care what others think about him, which leads to what is a healthy relationship between the pair. This forces Rosie to think of their relationship differently.

The movie removes the restraints age puts on love and makes for a wholesome, heartwarming, and hilarious watch. Many believed Michelle Pfeiffer and Paul Rudd made the perfect onscreen pair. The movie proved to be a hit with many like mitchkramer expressing that “with a cast of Paul Rudd, Michelle Pfieffer, Saoirse Ronan […] how could it be bad?” whilst also changing the way age gaps are shown in the world of romantic comedies.

2 The Proposal (2009)

Margaret and Andrew sit awkwardly

Andrew Paxton is one of Ryan Reynold’s best roles to date with the movie employing the fake dating-to-dating trope alongside some seriously hilarious scenes but it was the chemistry between the pair that left fans completely captivated. Whilst the movie never made a huge deal about the age gap between them, fans like MarcDuan noticed that “he was her PA, so clearly it was implied her character [was] at least 10 years his senior.”

The relationship between the two symbolized this very subtly by Margaret being much more put together than Andrew. But in the end, the iron sheet that sought to protect her from love was melted away. The pair’s onscreen chemistry mirrored in their healthy relationship which developed between them.

1 Harold And Maude (1971)

Harold and Maude kissing

Harold And Maude are 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 huge age gap. The couple grasps the attention of viewers and highlights what a healthy relationship looks like.

Maude helped Harold move away from his somewhat boring life whilst Harold helped 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. Fans like Uranus_Hz claim that “everyone should see this film.”

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