Buzz
Many films explore May-December relationships, where the age difference often shapes the dynamics between the characters. However, some of these pairings stand out as particularly strange, either due to a massive age gap or other factors that make them seem mismatched in unexpected ways. These are 10 of the most bizarre May-December movie romances in cinematic history.
10. Cactus Flower (1969)
The quirky romantic comedy Cactus Flower, based on the successful Broadway play, features Walter Matthau as Dr. Julian Winston, a middle-aged dentist who enjoys his independence so much that he pretends to be married to avoid commitment. When his latest girlfriend, the eccentric 21-year-old record store clerk Toni Simmons (Goldie Hawn), attempts suicide over her fear of a future without him, Julian tells her he and his wife are divorcing.
Toni agrees to marry him but insists on meeting his estranged wife first. This forces Julian to ask his long-time dental assistant, Stephanie Dickinson (Ingrid Bergman), to impersonate his wife. Unbeknownst to Julian, Stephanie has secretly been in love with him. As the farcical story unfolds, Julian must choose between the much younger Toni and the more mature and age-appropriate Stephanie.
Although the ending is fairly foreseeable, the adventure itself remains an enjoyable ride that brings a refreshing twist to the usual May-December-themed movies.
9. As Good as It Gets (1997)
The romantic comedy As Good as It Gets is a quirky tale from every perspective. Directed by James L. Brooks, the film showcases a diverse ensemble of characters who are brought together on a bizarre and humorous road trip. Jack Nicholson delivers a standout performance as Melvin Udall, a middle-aged, misanthropic, bigoted, and highly unlikely romance novelist. He forms an unexpected bond with Carol Connelly (Helen Hunt), a young single mother who works as a waitress at Melvin's regular diner. Despite his rude demeanor and severe OCD, Carol is the only waitress who can tolerate him.
When Melvin unexpectedly shows kindness by helping Carol secure medical treatment for her ailing son, she begins to see him in a new light. Later, when his neighbor, a gay artist named Simon Bishop (Greg Kinnear), is attacked, Melvin reluctantly agrees to look after Simon’s dog and, eventually, drives him from New York to Baltimore to seek financial help from Simon’s estranged parents. Carol accompanies them on the journey.
The trip is far from smooth, but Melvin begins to show signs of personal growth. Despite his abrasive personality, a subtle May-December romance begins to unfold between him and Carol.
8. Sunset Boulevard (1950)
In Billy Wilder's legendary film, Sunset Boulevard, the age gap of 20 years between 30-year-old struggling screenwriter Joe Gillis (William Holden) and 50-year-old washed-up silent film star Norma Desmond (Gloria Swanson) is not particularly extraordinary when compared to other May-December movie couples. However, the real challenge facing Joe and Norma is not their age difference, but Norma’s unstable mind. This mental deterioration is what turns the film from a dark comedy into a devastating tragedy. After Joe moves into her mansion to work on a screenplay, he becomes her lover of sorts. Although Joe eventually develops feelings for Norma and remains with her out of concern for her, he is the one who truly faces danger. When Joe decides to escape her delusional world and return to his old life, Norma takes his life as he tries to leave her behind.
The central issue in Sunset Boulevard isn't simply the age gap between Joe and Norma, but rather Norma’s unraveling sanity. This insanity is what transforms the film’s tone from dark humor to tragic sorrow. After Joe moves in to assist with her screenplay, he becomes entangled in a complex relationship with Norma, eventually staying out of care for her. However, the true danger lies in Joe’s decision to leave, which leads to his untimely death at the hands of the delusional Norma, as he attempts to walk away from her world.
7. Breezy (1973)
Clint Eastwood's directorial debut, Breezy, stars William Holden and Kay Lenz as an unlikely May-December couple, offering a poignant look at their mismatched romance. This film stands out for several reasons: it marks Eastwood’s first foray behind the camera, features a memorable soundtrack by Michel Legrand, and portrays the contrasts between the WWII generation and the hippie culture. Holden, who played the 'May' in Sunset Boulevard two decades earlier, switches roles in Breezy, now embodying the 'December' of the relationship.
Breezy is a story about a free-spirited, essentially homeless young woman (Lenz) who crosses paths with Frank Harmon (Holden), a cynical, middle-aged divorced businessman. He reluctantly offers her a place to stay, and despite their stark differences, a romance blossoms between them. Though it seems unlikely to endure, the couple decides to live in the moment and enjoy their time together, knowing that their relationship is likely short-lived.
6. Alex & the Gypsy (1976)
The vibrant romantic comedy Alex & the Gypsy, adapted from Stanley Elkin's novel The Bailbondsman, stands out for a variety of reasons. One of the more striking elements is the considerable age gap between the two protagonists, though this seems almost secondary given the complexities of their relationship.
First, viewers must come to terms with Jack Lemmon playing a rather unsavory bail bondsman, which is a departure from his usual roles. The plot itself stretches the imagination as well. Alex (Lemmon) and Maritza (Geneviève Bujold), a young gypsy woman, have a history. Years earlier, Alex helped her escape an arranged marriage. After their breakup, Maritza reappears in his life, needing his assistance to post bail after she kills her abusive boyfriend.
The age difference between Alex and Maritza—17 years in real life—emphasizes their apparent incompatibility, which is less about age and more about their contrasting cultural backgrounds. While Alex is grounded in a more conventional life, with his job and home, Maritza yearns for freedom and a more nomadic lifestyle, which reflects her gypsy heritage.
5. Blame It on Rio (1984)
The film Blame It on Rio strikes a balance between bizarre humor and shocking moments. It tells the story of 43-year-old Matthew Hollis (Michael Caine), who embarks on a brief affair with his friend Victor’s young daughter, Jennifer (Michelle Johnson), while vacationing in Rio with their families. Although Jennifer's exact age is never stated, she appears to be in her late teens—Johnson was 18 at the time of filming. Despite the provocative plot, Caine’s portrayal of the well-meaning but conflicted Matthew prevents him from coming across as overly predatory.
At the outset of the film, Matthew is blindsided by the revelation that his wife Karen (Valerie Harper) wants a break from their marriage and plans to go on a separate vacation. His confusion only grows when he is approached by Jennifer, who confidently pursues him on the beach. Afterward, Matthew struggles with overwhelming guilt as he tries to resist Jennifer’s advances and prevent Victor (Joseph Bologna) from discovering the affair.
Eventually, Matthew discovers that two people he was concerned about, Karen and Victor, have been secretly having an affair. As Matthew and Jennifer entertain the idea of running away together, convinced they are in love, the reality is that their relationship is fraught with incompatibility. The awkwardness is amplified by the fact that Matthew has known Jennifer since she was a child, making their situation even more unsettling.
4. Obsession (Circle of Two) (1981)
It is crucial to clarify from the outset that there was no actual physical relationship between the 60-year-old artist Ashley St. Clair and the 16-year-old schoolgirl Sarah Norton, who falls hopelessly in love with him during the Canadian film Obsession (originally titled Circle of Two).
Although Ashley, portrayed by Richard Burton, eventually confesses his love for Sarah (Tatum O'Neal), he declines to become physically involved with her, despite Sarah's relentless attempts, such as when she unexpectedly disrobes while he paints her portrait. Their romance remains unreturned, but the film is still quite unsettling, largely due to the contrast between Burton’s jaded character and O'Neal's youthful innocence, representing extreme opposites of their respective age groups.
At one point, Sarah runs away from home to pursue Ashley in New York, but he convinces her that a relationship between them would end disastrously. They come to an agreement to love each other from a distance. The film, based on Marie-Terèse Baird’s novel, received mostly negative reviews, partly due to its widely deemed unrealistic premise.
3. Harold and Maude (1971)
The unconventional dark comedy Harold and Maude, which explores the unlikely bond between a morbid 20-year-old man and a free-spirited 79-year-old woman, has achieved cult status. The film stars Bud Cort as Harold, a young man fixated on death, and Ruth Gordon as Maude, a lively, young-at-heart senior who meets Harold at a funeral and teaches him the true meaning of life.
The two characters dive into various adventures, eventually developing a romantic relationship. Harold and Maude is a film that tends to spark strong opinions—people either adore it or despise it. Upon its initial release, however, the response was largely unfavorable, partly due to its debut coming too late to be part of the 1960s counterculture. By the 1980s, the film had garnered a devoted cult following.
2. The Humbling (2014)
The romantic dramedy The Humbling, adapted from Philip Roth's novel, features Al Pacino as Simon, an aging actor struggling after a public breakdown during which he attempted suicide. His life grows even more complicated when he becomes entangled with Pegeen (Greta Gerwig), a younger woman confused about her sexuality, who happens to be the daughter of old friends.
Pegeen, who has never truly gotten over a childhood crush on Simon from when she was eight, reappears in his life after his release from a psychiatric facility. Their relationship is marked by an age gap that Simon finds increasingly difficult to manage, but the larger issue in the story is the complexity of their individual and shared emotional turmoil.
Before her involvement with Simon, Pegeen had been in relationships with a woman named Louise (Kyra Sedgwick) and a man, Prince, who had undergone gender reassignment surgery and now identifies as Priscilla (Billy Porter). Simon's social circle also includes some colorful figures, such as a socialite he met in the psychiatric hospital who is obsessed with convincing him to murder her husband.
If The Humbling feels reminiscent to moviegoers, it's likely due to its striking similarities to Birdman, particularly regarding Simon's struggle to revive his acting career. Christy Lemire from RogerEbert.com pointed out the unfortunate timing of The Humbling's release, coming just three months after the far superior Birdman, observing: 'It is a wild and unfortunate coincidence that The Humbling comes out three months after the vastly superior Birdman, and that it covers so much of the same territory through so many similar images, moments and beats.'
1. The Graduate (1967)
The Graduate, a classic satirical comedy based on Charles Webb's novel, isn't so much about a May-December romance but rather a May-December infatuation. Dustin Hoffman stars as Ben Braddock, an introverted young man fresh out of college, who begins an unconventional education through a forbidden relationship with Mrs. Robinson (Anne Bancroft), an older, married woman who is the wife of his father's business partner.
Ben, caught between his uncertainty about his future and a secret affair with a married older woman, finds himself in a chaotic situation. The confusion deepens when he further defies norms by becoming romantically involved with Elaine (Katharine Ross), the daughter of his lover.
Directed by Mike Nichols, The Graduate delves into themes such as hypocrisy, the loss of innocence, and the cultural upheavals of the 1960s. It proves to be as much a coming-of-age story as a tale about lust, with Ben eventually realizing that Elaine is the woman he truly loves. Ben, initially conventional, challenges the expectations of the Robinsons and society by disrupting Elaine's wedding to a man her parents have selected for her.
