25 Best Older Man Younger Woman Relationship Movies

If you look closely, almost half of the relationship films made in Hollywood and elsewhere are about older men and younger women. But, technically, most of those films don’t qualify for this list simply because even though there might be a huge gap between the ages of actors, the characters are presumed to be much closer in age. This list is specifically about the films where the age difference is acknowledged. Older man-younger woman relationship movies require special sensitivity since the film — and the filmmaker — can quickly be judged as creepy and predatory if the story is not handled appropriately. That’s why we have had very few good movies made on the subject, and the following make the cut.

25. Madrid, 1987 (2011)

Directed by David Trueba, ‘Madrid, 1987’ stars María Valverde, José Sacristán, Alberto Ferreiro and Ramon Fontserè. It tells the story of celebrated journalist Miguel, who agrees to sit for an interview with journalism student Ángela. While exploring different kinds of topics, including journalism, career, politics, literature, idealism, and more, Miguel takes a liking to Ángela. As the movie proceeds, things get more intense, both physically and philosophically. An authentic portrayal of a generational clash, ‘Madrid, 1987’ is a must-watch. You can stream the film here.

24. Sugar Daddy (2020)

‘Sugar Daddy’ is directed by Wendy Morgan and stars Kelly McCormack, Amanda Brugel, Aaron Ashmore, and Kaniehtiio Horn. It centers on Darren, a very talented singer-songwriter who struggles to produce her music by doing one job or another. She ultimately signs up on an online dating service and finds that it is easy money. However, her encounter with the rich, sophisticated, and ego-less elderly Gordon allows her to see life differently. Well-known for its visual elements and its music, you can stream ‘Sugar Daddy’ right here.

23. Elegy (2008)

Starring Ben Kingsley and Penélope Cruz, ‘Elegy’ is a romantic drama by Isabel Coixet. Based on Philip Roth’s 2001 novel ‘The Dying Animal,’ the movie revolves around middle-aged literature professor David Kepesh, whose self-proclaimed “emancipated manhood” state is compromised by one of his students, the beautiful Consuela Castillo. While his interactions with women are brief and more often sexual, Consuela enters the scene and changes his outlook seemingly forever. As he tries to seduce her, he questions his own life, including his son. Which way will he go? To find out, you can stream the film here.

22. American Beauty (1999)

Directed by Sam Mendes, the movie stars Mena Suvari, Kevin Spacey, Thora Birch, and Wes Bentley. The film centers on 40-something-year-old suburbanite Lester Burnham, who has what people call the “perfect life.” However, his wife is having an affair, his daughter dislikes him, and a midlife crisis is prevalent. As he struggles to handle all this, comes Jane’s classmate Angela Hayes, who springs within him a desire that he thought didn’t exist anymore. Infatuation creeps in, but isn’t it off-limits now? Does pursuing his new desires count as love? To know, you can stream the movie here.

21. Lust, Caution (2007)

This Ang Lee directorial is an erotic espionage that stars Tang Wei, Tony Leung, Joan Chen and Wang Leehom. It is based on Eileen Chang’s 1979 novella of the same name and is set in the first half of the 20th century in Japanese-occupied China. It revolves around how a theatre troupe hires Wong Chia Chi, a Hong Kong college student, to seduce and assassinate Japanese collaborator Mr. Yee. However, as time passes, feelings take over plotting and she finds herself struggling to carry on. Will she give up or continue the mission? What about the consequences if she gets caught? To find out, you may check out the film here.

20. The Girl on the Bridge (1999)

Patrice Leconte has directed this French film (French title: La fille sur le pont) that stars Daniel Auteuil and Vanessa Paradis. The movie explores an unlikely romantic relationship between a knife thrower named Gabor and a girl named Adèle, whom the former finds about to jump to her death from a bridge in Paris. A platonic relationship sprouts as they get to know each other and serve as each other’s companions in an otherwise dull and uncertain life. Luck, too, shines on them. However, unforeseen circumstances follow, and the two get separated; she goes to Greece, and he goes to Turkey, only to realize that they need each other and only that shall bring them luck. Will they be able to “bridge” the gap?

19. Guinevere (1999)

‘Guinevere’ is a forced-romance film centered around a melodramatic relationship between a 50-year-old Casanova photographer and a 20-something misfit, who becomes the photographer’s protégé in her search for attention from men. ‘Guinevere’ showcases the likelihood of young girls falling prey to the charm and affection of charismatic older men, but director Audrey Wells’ aesthetic direction has made this film a piece worth a watch. It follows the unusual and forced relationship between protagonist Harper Sloane (Sarah Polley) and Connie Fitzpatrick (Stephen Rea). Why forced?

Throughout the film, Connie is depicted as a man who can’t be trusted with his instincts and intentions unclear; however, Harper’s affection and love towards him force her to stay with him until she is confronted with his true self and the reality of his past relationships. The film, however, loses grasp over its intensity and elements of surprise, as it takes predictable terms, followed by a weakly and vaguely shot ending and climax (a result of a possible tight schedule and budget). Though Wells’ direction and Polley’s performance are a fantastic contribution to the film, the underdevelopment of supporting characters (especially that of Harper’s mother), loose construction of the storyline, and a not-so-enthusiastic ending diminish the film’s potential. You can watch the movie here.

Read More: Best ‘Orange is the New Black’ Sex Scenes

18. Noce Blanche (1989)

Nominated for three Cesar Awards, ‘Noce Blanche’ (English: ‘White Wedding’) is a French-language movie depicting the attraction, affection, and romance between a man and a considerably younger girl, which takes a pessimistic turn as their love for each other grows, crossing boundaries of societal trends and obligations. ‘Noce Blanche’ is a tale of 17-year-old Mathilde, whose loneliness caused by her father’s absence and her suicidal mother leads her into an exploitative state, leading her to fall for a married man in his later ages. As his presence begins to cure her solitude and isolation, her lack of sanity and sensibility causes her to become obsessed with her newly found love, which ultimately leads to the destruction of lives and many relationships.

‘Noce Blanche’ is an old man-younger woman relationship movie that follows a morally wrong storyline, showcasing what nauseating uncontrolled desires, seclusion, and stubbornness can do to the human mind. Vanessa Paradis plays Mathilde, who isn’t the film’s attention despite being the lead protagonist. Her major scenes depict her in a state of anguish, anger, and anxiety, which limits her acting and expressions. However, lead actor Bruno Cremer provides an astonishing portrayal of Francois, an intelligent man caught in a spell of irresistible compassion.

Read More: Best Outlander Sex Scenes

17. The Humbling (2014)

An aging actor trying to revive his career embarks on a relationship with his ex-girlfriend’s young daughter, which turns his life upside down. ‘The Humbling’ is one of the prominent highlights of actor Al Pacino’s filmography in his later years. Pacino plays Simon Axler, a broken and forgotten actor who is trying to regain his identity among the viewers through Broadway, but his stage fright and fear of self-presentation prevent him from doing so. Confronted by the horrors of his past, Axler finds a fine support in his “goddaughter” Peegen. The film then revolves around the lives of these two characters, which takes a new turn when they embark on an unexpected relationship. The conclusion set on a Broadway stage gives the viewers an ordinary but astonishing end to the story.

‘The Humbling’ deserves appreciation for its new take on a romantic drama. After a series of shortcomings, ‘The Humbling’ is a fair revival of Al Pacino’s career, who had been looking for a way to get back in the world. Not a blockbuster, ‘The Humbling’, however, deserves an audience. Feel free to check out the movie here.

Read More: Best Game of Thrones Sex Scenes

16. My First Mister (2001)

‘My First Mister’ chronicles the story of a troubled teen, Jennifer, a gothic-styled girl struggling to live by the norms of society. As she graduates, she is given a job by Randall Harris, a clothing store owner. As she tries to adopt the reality of her life, she finds solace in the pieces of advice and experience of a mature and realistic Randall, forming an unusual friendship with him.

For how ‘My First Mister’ is an inclusion to the list, the answer is that the old man-younger woman relationship here is not the bond of love but the bond of friendship. Albert Brooks (who is known for his later role in ‘Drive’) plays Randall Brooks, a divorcee living an isolated and monotonous life, while Leelee Sobieski plays Jennifer, the teenager looking for answers to life. The film is worth watching for its focus on multiple teenage complexities, and it aesthetically depicts the human need and requirements of reaching out to a friend or a person who cares to see what life is about, in this case, what life has for one. Of all the romantic couples portrayed on-screen, this one is the endearing, sweetest, and sentimental kind. You can check out the film here.

Read More: Best Shameless Sex Scenes

15. Blue Car (2002)

Hollywood is known for films that bring out compelling results from the most basic and simple storylines. ‘Blue Car’ is one such movie which, despite many flaws, does not fail to impress the viewers with its enigmatic characters and the dynamic performances of the actors portraying them. ‘Blue Car’ is the story of a young teen Meg, who is awkwardly and uncomfortably attracted to her English teacher given their common interest and passion for writing. The film chronicles this teacher-student relationship as Meg prepares herself for a poetry contest, which drastically ends on a completely jaw-dropping node, providing an unexpected twist in the final plot.

The film maintains a strong A+ throughout its running time, taking its perfection and realism to another level in the last moments of the film. The cast here (David Strathairn and Agnes Bruckner) gives outstanding performances to hold the film together. Considering it comes from a debut director, ‘Blue Car’ is one of the few films that pay that much attention to detailing and background exploration, which has made this film, despite the few flaws and quibbles, a remarkable cinematic experience. You can watch ‘Blue Car’ here.

Read More: Best Girls Sex Scenes

14. An Awfully Big Adventure (1995)

Despite not being a romantic film, ‘An Awfully Big Adventure’ is a baffling story of a young girl, Stella Bradshaw, who falls for a man considerably older than her while she tries to fulfill her sexual urges and desires by other means possible. Hugh Grant plays Meredith Potter, a homosexual and sadist director of the theatre group Stella works at, as well as the love interest of 16-year-old Stella. Alan Rickman plays O’Hara, an actor in his forties who falls for Stella but is eventually used by her for sexual benefits. As the story moves, the relationship between Stella and the two men begins to collapse due to Stella’s biased affection for Meredith despite his deeds and O’Hara’s deep concerns for her well-being.

The film is a complicated romantic triangle between the three protagonists, wherein the girl is a teenager while the men are considerably older than her. Though received moderately by the critics, the presence of names like Alan Rickman and Hugh Grant has made this film an interesting experience. The film isn’t a romantic folklore disguised as a British sadistic tale but is a sad and unpleasant theatrical filled with dark character elements and a jaw-dropping, but dissolute and unwanted ending. Based on Beryl Bainbridge’s novel of the same name, ‘An Awfully Big Adventure’ is a dark, metaphorical tale, admirable for its eccentricity blended with a subtle screenplay and awesome acting.

Read More: TV Shows With Most Nudity

13. Great Balls of Fire! (1989)

Here’s an outstanding biographical film depicting the life of rock and roll star Jerry Lee Lewis, with Dennis Quaid putting himself through a masterful performance in the shoes of this historical music icon of the 1950s. Amid his wild and electrical career, it is his marriage to his 13-year-old cousin that introduces the “Lolita Complex” and highly controversial occurrence that led to his near extinction from the musical scene. Known for his unquestionable musical talent and extroverted creativity, the darker and arrogant sides of his personality, together with his alcoholism, are also aspects shown in this movie, giving it a broad and varied insight into the life and mind of this piano master.

Read More: Best Nude Scenes of 2017

12. The Girl in the Café (2005)

A lonely and alone employee of Her Majesty’s Treasury under the Chancellor of Exchequer unexpectedly runs into an enigmatic lady of a much younger age than him. As the film’s events unfold, their sudden interaction grows into a stronger bond as they struggle to settle their differences concerning their views and opinions of the world.

‘The Girl in the Café’ is a romance cum social film, which has tried to highlight the third world issues and the negligence of nations like Great Britain towards the suffering population of these nations and their failure to aid them in the name of humanity. The film’s best part is that it never derails from its romance plot as these issues are not visualized but are discussed in conversation, thus keeping the characters’ individual plots intact. However, the unstructured screenwriting struggles between the humanizing message and the awkward romance between Laurence (Bill Nighy) and Gina (Kelly Macdonald).

The film’s success is a credit to Macdonald’s performance, which earned her an Emmy for Best Actress in a Limited Series or Television Movie. Winner of Outstanding TV Movie at Emmys, ‘The Girl in the Café’ is a pleasuring romance where an old man’s conscience is questioned by his younger female counterpart, giving a lovely closure.

Read More: HBO Shows With Most Nudity

11. Frank & Lola (2016)

A noir, dark, and witty psychological romance, ‘Frank & Lola’ is a stupendous depiction of male obsession and jealousy for the woman of his life. Intoxicated with violence, seduction, and sex, ‘Frank & Lola’ is a mesmerizing erotic thriller about Frank, an excessively possessive and obsessed chef in Las Vegas, and Lola, a newbie in town who happens to cross paths with Frank. The story then takes various twists and turns as the secret of this mysterious young woman is revealed slowly and gradually, which eventually forces Frank into fits of trauma triggered by a psychological compulsion.

‘Frank and Lola’ finds a great star in Michael Shannon, who profoundly showcases the versions of Frank’s character, which escalates from loving to violent, compulsive, possessive, and ultimately to broken and lonely. He is well supported by Imogen Poots, who proves her acting credibility, as well as her talent over many other actresses. Moreover, fine praise for director Matthew Ross, who successfully sustains a hit directorial debut that digs deeper into the perceptive observations of the viewers. You can stream ‘Frank & Lola’ here.

Read More: Best Taboo Movies

10. Circle of Two (1981)

This Canadian drama stretches out the age difference further than any other film on this list. This time, a tender 16-year-old girl who writes poems falls in love and commences an innocent yet quite emotional relationship with an older painter at the age of 60. It is a long and realistic portrayal of such an unsure and doubtful situation, yet it gives us a good insight into each character, making them very likable and truthful. With Richard Burton taking on the role of the painter and Tatum O’Neal the one of teenage Sarah Norton, this dramatic story takes on the controversial “Lolita Complex” and brings it into an everyday type of environment, where things might not even seem that difficult to accept when love is at the core of the character’s actions. You can stream it here.

Read More: Actors Who Went Nude For Movies

9. Quills (2000)

A critical blockbuster, ‘Quills’ is a semi-fictionalised biography of French philosopher and writer Marquis de Sade, who was known for his hedonist sexual lifestyle, which inspired his many erotic works, and also led him to years of incarceration and imprisonment. The film depicts the later years of his life in a French asylum, where he tries to battle the forced treatment for his ‘insanity,’ as well as his sexual compulsion and unwanted advances toward young women. In between this story about Sade and his psychological state is the young laundress Madeleine, who admires Sade’s work and is subsequently driven toward him out of love. Though this is a minor part of a much larger plot, the romance between Madeleine (played by Kate Winslet ) and Sade (played by Geoffery Rush) drew a lot of attention among film critics and audiences. The film’s depiction of nudity and sexual violence, though criticized, added to the realism in Philip Kauffman’s direction.

Besides Kauffman’s direction, ‘Quills’ marked Rush’s finest performance to date apart from the equally mesmerizing role of Hector Barbosa in ‘Pirates of the Caribbean.’ While Rush was at his best, Winslet left another spot of her perfection in ‘Quills’ within a short time of her Academy Award-nominated role in ‘Titanic’ (1997). Joining this team of flamboyants is Joaquin Phoenix as du Coulmier, the director of the asylum containing Sade. Du Coulmier is a man who is curious and somehow divided between his duties, his belief in Sade, and his words. Supported by a large ensemble, ‘Quills’ is a stylish and terrifyingly good period drama. You can check out the movie here.

Read More: Best Movies About Porn Industry

8. An Education (2009)

Now, this is a film set in Britain’s sophisticated, strict, and structured culture and lifestyle, wherein a teen’s desires to live a life of luxury, independence, and free will lead her to cross paths with a man much older than him, which turns out to be a lesson for her, giving her, the true education of life. The film is the story of a teen full of dreams, Jenny, whose one unusual encounter with David, a charming Englishman, leads her life towards a path of addictive love and affection, forcing her to lose her sense of truth, reality, and the care of her loved ones towards her.

Best Picture nominee at Oscars that year, ‘An Education’ is best known for the outstanding performance from lead actress Carey Mulligan, who passes with a fantastic charm, decency, and perfection in her acting, overshadowing the other forgettable performances, including that of actor Peter Sarsgaard. Carey Mulligan astonishingly portrays the teen protagonist and flawlessly executes the transformations in the characters’ beliefs and personalities as she learns step-by-step throughout the film.

Starring an ensemble, also including Dominic Cooper, Rosamund Pike, and Alfred Molina, ‘An Education’ is also known for its quite accurate and prolific setting of the 1960s British era, as well as for its setting of London city per the locations of that time. Despite three Academy Award nominations and a critically acclaimed performance from Mulligan, ‘An Education’ remains heavily underrated. You can watch the movie here.

Read More: Best Vintage Erotica Movies

7. Palo Alto (2013)

This was Gia Coppola’s (granddaughter of Francis Ford Coppola) feature film debut that brilliantly stars amongst others, Emma Roberts and James Franco. Amid the adolescent life and endeavors of a young group of teenagers, April (Roberts) and her soccer coach, Mr. B (Franco), become involved in a more intimate relationship than the usual student-teacher correlating approach should be. A greatly constructed and drifting storyline, with well-defined characters seen from a dreamy and reckless world created by beautifully stylized cinematography, achieves an open retrospective into these varied souls of Palo Alto. You may watch the film here.

Read More: Best Nude Scenes in Movies

 6. As Good As It Gets (1997)

Age is just a number for the great Jack Nicholson. The man defines charisma and just oozes class here in every frame he’s in. He was 60 when he did this film, but not for a moment did you feel any kind of awkwardness here when he was dating a 34-year-old Helen Hunt in the film. That’s what flamboyance and charisma are all about. ‘As Good As It Gets’ is a sweet little romantic comedy that tells the story of a misanthropic, annoying, obsessive-compulsive writer, played by Nicholson, who has to take care of his neighbor’s dog. He falls in love with a waitress, almost half his age, who is a single mother with a chronically ill son. The film beautifully establishes the characters and their relationships, taking its time to build the story. It’s wonderfully made with some fine performances by Nicholson and Hunt, both of whom won the Academy Award for Best Actor and Best Actress, respectively. Feel free to check out the movie here.

Read More: Best Movies Like Porn on Netflix

5. Last Tango in Paris (1972)

Bernardo Bertolucci’s magnum opus is one of the most controversial films ever made. The film focuses on a man recovering from his wife’s death who develops an anonymous sexual relationship with a much younger woman. The film is a profoundly liberating piece of pure erotic cinema that just melts you in its gorgeously painful depiction of the human condition. It’s so emotionally raw, dark, and tragic beyond words. The film has Marlon Brando deliver one of the greatest acting performances of all time. You can check out the film here.

Read More: Best Movies of All Time

4. Lolita (1962)

“How did they ever make a movie about Lolita?” says the movie poster. The film focuses mostly on the obsession towards the pretty and young 14-year-old flirtatious teenager, whom Humber Humbert is passionately unable to distance himself from. Although it omits much of the provocation the book contains, it was still seen as a very controversial film due to the subject, in general, being taboo and immoral in the eyes of the public. However, it was a total commercial success and has since marked its importance in the history of cinema. You can watch ‘Lolita’ here.

Read More: Movies Like Basic Instinct

3. Manhattan (1978)

The film centers around Woody Allen’s character, Issac, a divorced New Yorker who is in a relationship with a high school girl, Tracy. The problem is that Issac considers himself to be far too mature to be in a relationship with this little girl and so he ends up falling in love with a woman of his age, the mistress of his best buddy. But things don’t work out, and Issac soon realizes that Tracy is his true love and that she loves him with all her heart despite his arrogance and narcissism. But perhaps life is just a beautifully wrapped-up box of missed chances, and it’s this realization that makes ‘Manhattan’ so profoundly moving. You may watch it here.

2. Three Colors: Red (1994)

There is something so inexplicably magical about the way Kieslowski just strikes you on an emotional level. The film depicts the relationship between a young woman and a cynical old judge who spies on the people around him by listening to their conversations. At first, their worlds seem vastly different, but there’s something between them that would later develop into a deeply intimate bond. Their relationship isn’t explicitly romantic, but you do get a feeling that they could be lovers, and Kieslowski hints to us that in many scenes, most notably in that beautiful scene where Jean-Louis Trintignant’s character says goodbye to Valentine and they both place their hands on the car’s window before he drives away. It’s a simple scene but speaks volumes of the intimacy of their relationship. You may watch ‘Three Colors: Red’ here.

 1. Lost in Translation (2003)

‘Lost in Translation is a sweetly melancholic tale of love, loneliness, and ennui. The film depicts the relationship between a middle-aged American actor and a much younger American woman who meet in a hotel in Tokyo. They are seemingly lost in a world and culture so alien to them and begin to discover themselves in each other despite their age difference. These are two souls stuck in very different phases of life, and yet they seem to have some sort of a connection between them. Their relationship seems platonic, but it has a very ambiguous tone, and we could never really know what Bob whispered in Charlotte’s ear, and perhaps that’s the beauty of life. You can stream the film here.

Read More: Best Incest Movies