19 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 huge gap between the age of actors, the characters are presumed to be much closer in age. For instance, in every movie that features Tom Cruise, his love interest is typically played by someone in 20s. He himself is in his 50s. But obviously, in films, he always plays 30-something character (okay, on rare occasions, 40-something).

This list is specifically about the films where the age difference is acknowledged. Older woman-young man relationship movies are rarely made, but when they are made directors don’t have to worry about looking like perverts. But 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. Here’s the list of best movies about older man-younger woman relationship.

19. Guinevere (1999)

‘Guinevere’ is a forced-romance film, centred 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 liking from men. ‘Guinevere’ showcases the likelihood of young girls falling prey to the charm and affection of charismatic older women, but director Audrey Wells’ aesthetic direction has made this film a piece worth a watch. ‘Guinevere’ follows the unusual and forced relationship between protagonist Harper Sloane (Sarah Polley) and Connie Fitzpatrick (Stephen Rea). Why forced?

Throughout the film, Connie has been depicted as a man who can’t be trusted with his instincts and intentions unclear; however, Harper’s affection and love towards him forces her to stay with him until she is confronted with his true self and 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.

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18. Noce Blanche (1989)

Nominated for three Cesar Awards, ‘Noce Blanche’ 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 in 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 the old man-younger woman relationship movie, which follows a morally wrong storyline, showcasing how nauseating can uncontrolled desires, seclusion, and stubbornness can do to the human mind. Vanessa Paradis plays Mathilde, who actually isn’t the film’s attention despite being the lead protagonists. 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 for an astonishing portrayal of Francois, an intelligent man caught in a spell of irresistible compassion.

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17. The Humbling (2015)

An ageing 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 for the story.

‘The Humbling’ is though not a popular film, it 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.

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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 the 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 much 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 of 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 care to see what the life is about, in this case, what life has for one. Off all the romantic couples portrayed on-screen, this one is an endearing and sweetest and sentimental kind.

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15. Blue Car (2002)

Hollywood is known for films that bring out a compelling result 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, give 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 of an attention to detailing and background exploration, which has made this film, despite the few flaws and quibbles, a remarkable cinematic experience.

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14. An Awfully Big Adventure (1995)

Despite not 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 fulfil 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-yr old Stella. Alan Rickman plays O’Hara, an actor in his forties who fell 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 elder than her. Though received moderately by the critics, the presence of names likes 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 a 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.

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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 1950’s.  In the midst of 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.

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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 much younger age than him. As the film’s events are unfolding, their sudden interaction grows into a stronger bond as they struggle to settle with their differences concerning their views and opinions for 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 visualised but are discussed in conversation, thus, keeping the characters’ individual plot intact. However, the unstructured screenwriting struggling between the humanising 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.

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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 mesmerising 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 to into a series of 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 in series 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, a fine praise for director Matthew Ross, who successfully sustains a hit directorial debut which digs deeper into the perceptive observations of the viewers.

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10. Circle of Two (1981)

This Canadian drama stretches out the age difference further than any other films 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 gives us a good insight into each character, making them very likeable 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 every-day type of environment, where things might not even seem that difficult to accept when love is at the core of the characters’ actions.

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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 fights tries to battle with the forced treatment for his ‘insanity’, as well his sexual compulsion and unwanted advances towards young women. In between this story about Sade and his psychological state is the young laundress Madeleine admires Sade’s work and is subsequently driven towards 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 Geoffery Rush) drew a lot of attention among the film critics and audiences. The film’s depiction of nudity and sexual violence, was though criticised, added to the realism in Philip Kauffman’s direction.

Besides Kauffman’s direction, ‘Quills’ marked Rush’s finest performance till date apart from the equally mesmerising role of Hector Barbosa in ‘Pirates of Carribean’. While Rush was at his best, Winslet left another spot of her perfection in ‘Quills’ within a short time of her Academy-Award winning 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 and his belief in Sade and his words. Supported by a large ensemble furthermore, ‘Quills’ is a stylish and terrifyingly good period drama.

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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 leads her to cross path with a man much older than him, which turns out to be a lesson of life 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 an 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 personality, as she learns step-by-step throughout the course of 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 and was an unfortunate box-office failure.

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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. In the midst of the adolescent life and endeavours 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 a beautifully stylised cinematography, that achieves an open retrospective into these varied souls of Palo Alto.

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 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 is 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 who won the Academy Award for Best Actor and Best Actress respectively.

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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.

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4. Lolita (1962)

“How did they ever make a movie about Lolita?” says the movie poster. I don’t think there’s anything Stanley Kubrick wouldn’t do if he felt it right to be created. That’s exactly what happened with this 1962 release of the famous story of “Lolita”, starring James Mason and Sue Lyon as the two contentious “lovers”. It focuses mostly on the obsession towards the pretty and young 14-year-old flirtatious teenager, who 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 to the eyes of the public. However, it was a total commercial success and has since then marked its importance in the history of cinema.

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3. Manhattan (1979)

Woody Allen’s ‘Manhattan’ is a film that changed my understanding and perceptions of human relationships and the beautiful absurdities of human nature. Like any other Woody Allen film, this is so much more than just a cute little romantic comedy. The film centres around 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 matured 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 was his true love and that she loved 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.

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2. Three Colors: Red (1994)

There is something so inexplicably magical about the way Kieslowski just strikes you on an emotional level. ‘Red’ was my first ever Kieslowski film and I was completely in awe of its beauty. 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 us with 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.

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 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 happen to meet in a hotel in Tokyo. They are seemingly lost in a world and culture so alien so alien to them and begins 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. The beauty of unknown.

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