Most Similar Movies to Come September (1961)
If you are looking for movies like Come September (1961), you might like movies tagged with keyword : mogul, manager, teen boy, teen girl, chaperone, lover, madcap, lighthearted, amusing, tender, italy, villa, hotel, town, vacation, romantic dilemma, scam, generation gap, accident, unlikely friendship, love, discovery, transformation, 1960s .
A Summer's Tale (1996), Before Midnight (2013), Love Story (1970), 303 (2018), The Longest Week (2014), Before Sunrise (1995), Three Steps Above Heaven (2010) ... Let's take a look at the following list...

A Summer's Tale (1996)
While having strong romantic feelings for one woman, a young man finds himself being drawn to a few others.
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Before Midnight (2013)
We meet Jesse and Celine nine years on in Greece. Almost two decades have passed since their first meeting on that train bound for Vienna.
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Love Story (1970)
A boy and a girl from different backgrounds fall in love regardless of their upbringing - and then tragedy strikes.
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303 (2018)
Two university students gain insight into life and love as they get to know each other during a road trip across Europe.
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The Longest Week (2014)
Conrad (Jason Bateman) is helped by his old friend Dylan (Billy Crudup) and returns the favor by falling for Dylan's girlfriend Beatrice (Olivia Wilde).
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Before Sunrise (1995)
A young man and woman meet on a train in Europe, and wind up spending one evening together in Vienna. Unfortunately, both know that this will probably be their only night together.
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Three Steps Above Heaven (2010)
A privileged woman and a reckless man fall in love despite their different social classes.
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That Touch of Mink (1962)
A rich businessman and a young woman are attracted to each other, but he only wants an affair while she wants to save herself for marriage.
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Forget Paris (1995)
Mickey, an NBA referee, meets Ellen, an American airline official, in Paris. It develops into a relationship of ups and downs.
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Rome Adventure (1962)
Under fire for giving a student her copy of a romance novel, Prudence resigns from her teaching position and sails for Italy.
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Nights in Rodanthe (2008)
A doctor, who is travelling to see his estranged son, sparks with an unhappily married woman at a North Carolina inn.
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The Butcher's Wife (1991)
A clairvoyant impulsively marries a butcher, moves to New York City and has a positive impact on the people she meets, changing their futures...which in turn changes hers.
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The Music Man (1962)
Harold Hill poses as a boys' band leader to con naive Iowa townsfolk.
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Kuch Kuch Hota Hai (1998)
During their college years, Anjali was in love with her best-friend Rahul, but he had eyes only for Tina. Years later, Rahul and the now-deceased Tina's eight-year-old daughter attempts to reunite her father and Anjali.
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Love Actually (2003)
Follows the lives of eight very different couples in dealing with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London, England.
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Romeo and Juliet (1968)
When two young members of feuding families meet, forbidden love ensues.
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Enchanted April (1991)
Four English women, after World War I, who are unhappy with their lives, and their time away on vacation in a beautiful Italian villa.
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