10 Weirdest May-December Movie Romances

There have been many May-December romances depicted in film. The impact that the age gap has on the relationship often depends on the personalities of the two characters. But in some cases, these pairings are very strange, either because of a shockingly large number of years between them or because there are other things, in addition to the age difference, that make them an odd match overall. These are 10 of the weirdest May-December movie romances of all time.

Related: 10 Movies That Were Ahead of Their Time

10 Cactus Flower (1969)

The kooky romantic comedy Cactus Flower, based on the hit Broadway play, stars Walter Matthau as swinging, middle-aged dentist Dr. Julian Winston, who likes his freedom so much that he pretends to be married so the women he dates won’t expect him to make a commitment. When his latest girlfriend, the flaky, 21-year-old record store clerk Toni Simmons (Goldie Hawn), attempts suicide because she doesn’t think they have a future together, he reacts by telling Toni he and his wife are divorcing.

Toni agrees to marry him but wants to meet his estranged wife first. This prompts Julian to ask his longtime dental nurse, Stephanie Dickinson (Ingrid Bergman), to pose as his wife. However, Stephanie is secretly in love with Julian. As the farcical story goes on, Julian has to make a difficult choice between Toni and the very attractive but much more mature and age-appropriate Stephanie.

Though the outcome is fairly predictable, it is an entertaining journey that offers an interesting twist on the typical May-December-themed films.^[1]

9 As Good as It Gets (1997)

The romantic comedy As Good as It Gets is an offbeat story from any angle. This James L. Brooks-directed film features an eclectic group of characters who are ultimately thrown together on a strange and humorous road trip. In one of his most memorable roles, Jack Nicholson plays middle-aged, bigoted misanthrope and unlikely romance novelist Melvin Udall, who befriends Carol Connelly (Helen Hunt), a young single mom who waits tables at a diner Melvin frequents. Because of his rudeness and his severe OCD, Carol is the only waitress who can get along with him.

After Melvin shows uncharacteristic kindness by helping Carol get medical treatment for her chronically ill son, she starts to see him in a different light. When his neighbor, a gay artist named Simon Bishop (Greg Kinnear), is assaulted, Melvin grudgingly agrees to take care of his dog and later drives him from New York to Baltimore to ask his estranged parents for financial help. Carol goes with them.

The journey is less than harmonious, but Melvin does start to grow. Despite his caustic behavior, a tentative May-December romance between him and Carol begins to blossom.^[2]

8 Sunset Boulevard (1950)

The twenty-year age difference between 30-year-old down-on-his-luck screenwriter Joe Gillis (William Holden) and washed-up 50-year-old silent film legend Norma Desmond (Gloria Swanson) in Billy Wilder’s classic Sunset Boulevard is not particularly shocking compared to some of the other May-December movie couples. Nor was it the biggest obstacle in Joe and Norma’s path.

Their main problem was sanity, or rather Norma’s lack of it, which was also what ultimately turned this black comedy into a tragedy. After Joe moves into Norma’s house to rewrite a screenplay for her, he becomes a sort of gigolo. He does eventually develop feelings for Norma and stays because he is concerned about her well being. However, he’s the one who’s really in danger. When he makes up his mind to leave her delusional world for his former life, Norma kills him on his way out.^[3]

7 Breezy (1973)

The romantic drama Breezy, starring William Holden and Kay Lenz as a completely mismatched May-December couple, is notable for a number of reasons: It was Clint Eastwood’s feature film directorial debut, the classic soundtrack was by Michel Legrande, and it was touted for how well it defines the contrasts between the WWII generation and the hippies. Holden went from being the “May” in Sunset Boulevard two decades earlier to the “December” in this film.

Breezy is about a free-spirited, essentially homeless young girl (Lenz) who becomes involved with Frank Harmon (Holden), a cynical middle-aged divorced businessman, after he reluctantly agrees to give her a place to stay. The two are so opposite that their romance seems doomed from the start. Seeing how unlikely it is that the relationship will survive long-term, the pair finally decide to just enjoy one another for as long as it lasts.^[4]

6 Alex & the Gypsy (1976)

The colorful romantic comedy Alex & the Gypsy, based on the novel The Bailbondsman by Stanley Elkin, is unusual in so many ways that the significant age difference between the two leading characters almost seems like a minor point.

First, we have to accept Jack Lemmon as a sleazy bail bondsman, which isn’t easy despite his impressive acting skills. The story itself requires a real stretch of the imagination as well. This is actually the second time around for Alex (Lemmon) and young gypsy woman Maritza (Geneviève Bujold), who is his former mistress. The two originally got together, as we learn in flashback, when Alex helped Maritza to avoid an arranged marriage. She eventually left him, and then, years later, she appears in his life again when she needs him to bail her out of jail after she kills her abusive boyfriend.

The difference in their ages—17 years in real life—accentuates their seeming incompatibility, which is more rooted in their cultural contrasts, with the middle-aged Alex tied to his job, home, and more traditional lifestyle, while Maritza craves freedom and the sort of nomadic existence that is familiar to her.^[5]

5 Blame It on Rio (1984)

The comedy Blame It on Rio is as wacky as it is shocking. The movie follows 43-year-old Matthew Hollis (Michael Caine), who has a fling with his friend Victor’s young daughter, Jennifer (Michelle Johnson), while their families are vacationing together in Rio. Jennifer’s age is never specified, but she seems to be in her late teens—Johnson was 18-years-old when the film was made. As outrageous as the premise sounds, Caine is so convincing in the role of the hapless Matthew that he does not come across as predatory.

At the beginning of the film, Matthew is completely blindsided to learn that his wife Karen (Valerie Harper) is dissatisfied with their marriage and wants to take separate vacations. He is similarly stunned by the advances of the sexually confident Jennifer on the beach one night. Racked with guilt afterward, he spends the remainder of the trip mainly trying to resist Jennifer’s efforts to continue the affair and keep Victor (Joseph Bologna) from finding out about it.

However, Matthew eventually learns that two of the people he was worried about hurting, Karen and Victor, have been carrying on an affair of their own. While Matthew and Jennifer believe that they are in love and consider running away together, it is obvious that they are not compatible. The fact that he has known her since she was a baby adds to the weirdness of the concept.^[6]

4 Obsession (Circle of Two) (1981)

It’s important to note up front that there was no real physical relationship between the 60-year-old artist Ashley St. Clair and 16-year-old schoolgirl Sarah Norton, who falls desperately in love with him during the Canadian film Obsession (originally titled Circle of Two).

Although Ashley, played by Richard Burton, eventually admits that he is in love with Sarah (Tatum O’Neal), he refuses to go to bed with her, despite Sarah’s best efforts, like when she suddenly decides to take off all her clothes while he is painting her portrait. Their romance is unrequited, but this movie is still pretty creepy, partially because the world-weary Burton and the child-like O’Neal both represent such extreme versions of people in their respective age groups.

At one point, she runs away from home to follow Ashley to New York, but he succeeds in explaining why a relationship between them would be disastrous, and they agree to love each other from afar. The movie, based on Marie-Térèse Baird’s novel, was mostly panned by critics, in part because of what was largely considered to be an unrealistic premise.^[7]

3 The Graduate (1967)

Iconic comedy satire The Graduate, based on the novel by Charles Webb. is not so much about May-December romance as May-December lust. Dustin Hoffman plays the introverted Ben Braddock, who has recently graduated from college and is now beginning a very different kind of education, thanks to predatory seductress Mrs. Robinson (Anne Bancroft), the middle-aged wife of his father’s business partner.

Between the uncertainty about his future and the clandestine affair with a married older woman, it is a very confusing time for Ben. Still, things get even crazier when he breaks another taboo by becoming romantically involved with his lover’s own daughter, college student Elaine (Katharine Ross).

The Mike Nichols-directed movie, which explores themes like hypocrisy, loss of innocence, and even the sixties counterculture, turns out to be as much about growing up and life lessons as it is about sex. Realizing Elaine is the woman he loves, Ben, who is so conventional at the beginning of the movie, rebels against not only the Robinsons, who are trying to keep them apart but society in general by stopping Elaine’s wedding to a man her parents have chosen for her.^[8]

2 The Humbling (2014)

The romantic dramedy The Humbling, based on the novel by Philip Roth, stars Al Pacino as Simon, an aging stage actor who is going through a very turbulent time following a public breakdown during which he tries to commit suicide. His life becomes even more complicated when he gets involved with the much younger, sexually confused Pegeen (Greta Gerwig), the daughter of some old friends.

Pegeen has apparently never gotten over the crush she developed on Simon almost three decades earlier when she was eight years old. This results in a visit from the adoring but manipulative young woman following Simon’s release from a psychiatric facility. While the vast difference in their ages is definitely an issue, with Simon struggling to keep up with Pegeen, the May-December aspect of the story is often overshadowed by all the other things these two characters are going through, both individually and as a couple.

Before she was with Simon, Pegeen had been in a lesbian relationship with Louise, played by Kyra Sedgwick, and with a man named Prince, who used to be Priscilla (Billy Porter), before his gender reassignment surgery. Simon has some interesting people in his life as well, including a socialite he met in the psychiatric facility who keeps trying to convince him to kill her husband.

If The Humbling seems familiar to movie fans, it may be because it has a lot in common with Birdman, especially in terms of what Simon is going through in trying to revive his career. As Christy Lemire of RogerEbert.com observed: “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.”^[9]

1 Harold and Maude (1971)

The offbeat dark comedy Harold and Maude, about the friendship/romance between a morbid 20-year-old man and a free-spirited 79-year-old woman, has become a cult classic. The movie stars Bud Cort as Harold, an eccentric young man with a death fixation, and Ruth Gordon as Maude, a wild, young-at-heart senior citizen who meets Harold at a funeral and really teaches him how to live.

The two get into all sorts of mischief and eventually become lovers. Harold and Maude is the kind of movie that people either passionately love or passionately hate. Still, when it was first released, the reaction was mostly negative, which is partially blamed on the film coming out too late to be part of the 1960s counterculture movement. By the early eighties, the film had gained a strong cult following.^[10]