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VOICE OVER: Phoebe de Jeu WRITTEN BY: B Stevenson
The leads have age differences, but these romance movies are for the ages. For this list, we'll be looking at romantic films that explore relationships with notable age gaps. Our countdown includes "All About Eve," "Lost in Translation," "Prime," and more!

#10: “All About Eve” (1950)

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This classic film concerns a relatively minor age difference that becomes a rather major cause for concern. The legendary Bette Davis plays Margo Channing, a Broadway actress worried about aging out of the business. Margo takes on a devoted fan named Eve as her assistant, but quickly regrets the decision. You see, Margo is insecure about the eight-year age gap between her and her boyfriend Bill. It’s not long before the much younger Eve makes a move on him. Fortunately, Bill remains devoted to Margo, and they even get engaged. There’s a reason this movie is ageless.

#9: “How Stella Got Her Groove Back” (1998)

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Angela Bassett stars in this beloved rom-com as Stella Payne, a high-powered trader living a comfortable life in San Francisco. Unfortunately for Stella, her love life is lacking. So, when her best friend persuades her to take a vacation, it’s off to Jamaica they go! This is where Stella meets an alluring stranger exactly half her age. Sure, they have incredible chemistry, but is their relationship really sustainable? It’s the question the couple dances around for nearly the entire film. Regardless of their future status, we simply loved seeing a hard-working woman have some much deserved fun.

#8: “Lost in Translation” (2003)

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Two individuals questioning their sense of belonging connect in a major way in this romantic comedy-drama from Sofia Coppola. Bob Harris is past his prime in show business and takes a promotional gig in Tokyo. While there, he encounters beautiful newlywed Charlotte. With both unaccustomed to their environment and unsatisfied in their relationships, the duo finds comfort in one another. While exploring the city, they also delve into the particular identity crises of young adulthood and middle age. It’s arguably an all too-common trope to have an older male character find love with a much younger woman. However, the connection between this specific pair feels wholly authentic.

#7: “Something’s Gotta Give” (2003)

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Screen legends Jack Nicholson and Diane Keaton light up the screen in this opposites-attract rom-com. Although they make for an age-appropriate couple, they aren’t together for the vast majority of the film. Rather, aging womanizer, Harry Sanborn, starts out dating playwright Erica Barry’s twenty-something daughter. In fact, he makes it a rule to date “much younger.” But, when Erica helps to take care of Harry after a heart attack, things get complicated. And, despite other (younger) romantic prospects, their attraction just can’t be ignored. Quite frankly, few films have explored love between generations with so much humor and wit as this one.

#6: “Hello, My Name is Doris” (2015)

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This romantic comedy-drama sees Sally Field shine as a kooky middle-aged singleton who develops a serious workplace crush. Doris Miller has worked the same job for ages and lives a hum-drum life on Staten Island. While grieving her mother and clashing with her brother, Doris finds an escape in the form of John Fremont, an attractive new addition to her company. While the two strike up a friendship, it’s clear that they’re not on the same page - Doris is very much smitten, while John is absolutely oblivious. Although the relationship takes a nosedive, the end of the film leaves some hope for the duo’s future.

#5: “The Reader” (2008)

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Kate Winslet won an Academy Award for her portrayal of a woman guilty of terrible crimes in this romantic drama. In 1958 Berlin, Hanna Schmitz initiates an extremely questionable sexual relationship with 15-year-old Michael Berg. Several years after her sudden disappearance, however, Michael is stunned to see her standing trial in a war crimes case. As it turns out, Hanna was a guard at a Nazi-run concentration camp during World War II. The pair maintains a relationship through Hanna’s imprisonment, but her past actions weigh heavily on Michael. The film’s tenuous age-gap romance certainly reflects broader themes of power, culpability, and the passage of time.

#4: “Middle of the Night” (1959)

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The central romance in this drama is complicated by a 30-year-plus age difference, not to mention an existing workplace dynamic. Office worker Betty is in her 20s and is already divorced. After her 56-year-old boss, Jerry, asks her out, the two strike up a fling. Betty is naturally conflicted, but she isn’t the only one - the pair’s families also have harsh feelings about their love. While Jerry’s relatives think his girlfriend is a gold digger, Betty’s mother isn’t thrilled in the slightest. Despite the pressure they face from outside forces, both lovers simply want to do what makes them happy. And at the end of the day, no one can argue with that.

#3: “Prime” (2005)

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Relationships can be complicated — but they’re rarely THIS complicated. Uma Thurman stars as Rafi Gardet, a divorcée in her late thirties with a flourishing career. Against her better judgment, she sparks up a romance with a 23-year-old painter, David. Lovestruck, Rafi proceeds to tell all to her therapist, Lisa. But, little do any of them know, Lisa is David’s mom. Although this is the most obvious obstacle to this burgeoning couple’s relationship, it’s not the biggest. While Rafi wants a child, she doesn’t want David to sacrifice his art in order to start a family. Considering the couple’s electric chemistry, it’s a truly heartbreaking conclusion.

#2: “The Graduate” (1967)

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This celebrated film follows an intergenerational affair between a recent college grad and a much older housewife, played by Dustin Hoffman and Anne Bancroft respectively. Over the course of a summer, Benjamin Braddock embarks on an illicit relationship with Mrs. Robinson, the spouse of his father-in-law’s colleague. At the same time, however, he reluctantly begins dating her daughter Elaine. The interplay between his two romances is fascinating to watch, with Benjamin’s feelings for the two women drastically changing over the course of the film. Although this romantic comedy-drama isn’t dark by any means, it does reveal how a hush-hush fling can quickly go south. Before we unveil our top pick, here are a few honorable mentions. “40 Carats” (1973) 40-Year-Old Ann’s Summer Fling Is Only 22, but He’s Not Going Anywhere “The Rebound” (2009) A 15-Year Age Difference Drives a Couple Apart, but Will They Reconnect Down the Line? “Call Me by Your Name” (2017) 17-Year-Old Elio & Graduate Student Oliver Fall in Love During a Summer in Italy “Rushmore” (1998) High Schooler Max & His Much Older Friend Both Fall for a First-Grade Teacher “White Palace” (1990) A Steamy Relationship Across Boundaries of Age & Class

#1: “Harold and Maude” (1971)

This coming-of-age comedy-drama concerns the May-December romance of May-December romances. 19-year-old Harold has a morbid fascination with death that disturbs his mother ― can you blame her? During a funeral, Harold meets the cheerful Maude, a woman who is a whopping 60 years his senior. Her optimistic perspective gradually rubs off on the grim youngster and they soon begin a love affair. It’s not exactly shocking that the people in Harold’s life are appalled at this news. But, when it comes to learning the importance of living life to its fullest, we suppose you should take the lesson where you can get it.

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