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May-December Romance Movies

21 Times There Was a MAJOR Age Gap in a Romance Movie

Everyone's a little fascinated with the unconventional. So it's no surprise that plenty of films have pushed the boundaries of the norm (and sometimes even of the appropriate or legal) to explore relationships that are outside of the box. While some of these May-December romances are entirely on the up and up, others definitely cross the line (we're looking at you, Lolita). We've rounded up some of the most notable romances that portray relationships with significant age differences: some are sexy, some are a little shady, and some are just downright wrong.

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1. American Beauty

YOU know the scene. The infamous rose-petals-in-the-bathtub-and-inappropriate-fantasies-from-an-ubercreepy-Kevin Spacey scene? Yep, American Beauty definitely goes there.

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2. American Pie

American Pie influenced our culture in many interesting ways (I don't think band camp has been the same since . . .), but it is perhaps most famous for popularizing the acronym "MILF," as in, mother I'd like to f*ck. Enter Paul Finch, who seals the deal with the movie's MILF, aka "Stifler's mom."

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3. An Education

In this coming-of-age drama, a young schoolgirl played by Carey Mulligan is seduced by a charming older man (Peter Sarsgaard) who isn't exactly the person he portrays himself to be.

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4. The Graduate

This film wrote the book on May/December romance: "Mrs. Robinson" is basically synonymous with "cougar." The Graduate is a film about a young college graduate's seduction by an older woman and friend of his father's. He then eventually finds himself falling in love with his lover's daughter. Very juicy.

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5. Harold and Maude

The story of Harold and Maude may not necessarily be a sexy one, but it's definitely the sweetest. A boy who is obsessed with death strikes up a friendship, and eventually a romantic relationship, with a 79-year-old woman who teaches him what a true gift life is.

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6. Liberal Arts

Elizabeth Olsen and How I Met Your Mother's Josh Radnor star in this romantic drama about a young college student's blossoming relationship with her university's much older admissions officer.

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7. Lolita

One of the most infamous and controversial film adaptations of all time (and rightfully so), Lolita follows the story of a man named Humbert Humbert who marries an adult woman in order to be closer to her young daughter, whom he nicknames Lolita. After his wife's death, Humbert is free to pursue his stepdaughter, and everything weirdly and grossly spirals out of control from there.

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8. Lost in Translation

In this dramatic comedy, an ageing actor bonds with a young college graduate after the two meet at a hotel in Tokyo. While nothing major happens between the characters Bill Murray and Scarlett Johansson play in Lost in Translation, there is an undercurrent of romance between the two — who are both in relationships with others.

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9. The Lifeguard

In The Lifeguard, Kristen Bell plays a 29-year-old disillusioned writer returning home after a difficult breakup. While working as a lifeguard at her old neighbourhood pool, she befriends and subsequently begins a (very inappropriate) romantic relationship with a teenage boy from the town.

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10. The Reader

This dramatic period piece starring Kate Winslet depicts a young boy and a former German SS guard as they develop a relationship over a shared love of books. The Reader chronicles the ramifications of the relationship as well as the consequences of the actions of the former guard prior to, during, and after their time as lovers.

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11. Wild Things

This erotic thriller is wildly over the top and controversial in countless ways — namely in its portrayal of a high school guidance counselor's sexual relationship with not one, but two students.

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12. Fish Tank

This British drama stars a super sketchy Michael Fassbender, whose character has a sexual relationship with his girlfriend's troubled 15-year-old daughter.

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13. Y Tu Mamá También

This coming-of-age movie is about two teenage boys who take a road trip with an older woman, and both end up having sexual relations with the woman and with each other.

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14. White Palace

A young widower, played by James Spader, falls for an older woman (Susan Sarandon), who is his waitress at a burger joint. In this romantic drama, the two must overcome their own personal tragedies in order to make room for each other in their lives.

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15. Magic in the Moonlight

Colin Firth plays an older man entangled with a younger woman — this time, a woman who claims to be a clairvoyant and a mystic — in Woody Allen's romantic comedy Magic in the Moonlight.

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16. My Tutor

Well . . . the title kind of speaks for itself here. A high school graduate on a quest to lose his virginity becomes involved with, you guessed it, his tutor, in this sexy comedy.

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17. The Piano Teacher

This erotic thriller's controversial subject matter deals with a sexually repressed piano teacher's sadomasochistic interests and her relations with one of her teenage pupils.

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18. Tadpole

A 15-year-old falls in love with his stepmother in this film that broaches not just the age taboo, but also touches on the incestuous taboo.

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19. How Stella Got Her Groove Back

Successful 40-year-old Stella's priorities shift as she rediscovers herself when she meets a man who is 20 years her junior on a much-needed holiday to Jamaica.

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20. Class

In a quest to have a successful sexual encounter, a young man finds himself involved with not one, but two much older women — one of whom is his roommate's mother.

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21. Seeking a Friend For the End of the World

Keira Knightley and Steve Carell star in Seeking a Friend For the End of the World, a romantic comedy about two people with quite a few years between them, who find love as an incoming asteroid threatens to destroy the world.

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