Best movies like Love and Pain and the Whole Damn Thing

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Flirting with Forty (2008)

Plot Summary:

A divorcee has a passionate affair with a much younger surfing instructor in Hawaii.

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I Could Never Be Your Woman (2007)

Plot Summary:

This movie follows a mother who falls for a younger man while her daughter falls in love for the first time. Mother Nature messes with their fates.

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In the Land of Women (2007)

Plot Summary:

After a bad breakup with his girlfriend leaves him heartbroken, Carter Webb moves to Michigan to take care of his ailing grandmother. Once there, he gets mixed up in the lives of the mother and daughters who live across the street.

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My Old Lady (2014)

Plot Summary:

Mathias Gold (Kevin Kline) is a down-on-his-luck New Yorker who inherits a Parisian apartment from his estranged father. But when he arrives in France to sell the vast domicile, he's shocked to discover a live-in tenant who is not prepared to budge. His apartment is a viager - an ancient French real estate system with complex rules pertaining to its resale - and the feisty Englishwoman Mathilde Girard (Maggie Smith), who has lived in the apartment with her daughter Chloé (Kristin Scott Thomas) for many years, can by contract collect monthly payments from Mathias until her death.

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A Month by the Lake (1995)

Plot Summary:

For 16 years Miss Bentley has been spending April at an elegant hillside villa on Lake Como. This year, 1937, her London society artist father has recently died and the only other English-speaking guests are brash Americans. Then Major Wilshaw arrives. He suggests they meet for cocktails and Miss Bentley stands him up -- not even thinking about it -- as she helps the new nanny of an Italian family settle in. Miss Beaumont, a tall, young American who has dropped out of finishing school in Switzerland, is bored and finds some amusement in flirting with the major, whose libido is awakened for the first time since before the great war. And Miss Bentley now finds more about the major to admire than his ears.

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How Stella Got Her Groove Back (1998)

Plot Summary:

Through good times and bad, Stella and Delilah have always had each other. Now, Stella's so busy building a life that she's forgotten how to really live. But Delilah is about to change all that. What starts as a quick trip to Jamaica, end as an exhilarating voyage of self discovery as Stella learns to open her heart and find love - even if it's with a man 20 years her junior.

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Prime (2005)

Plot Summary:

A career driven professional from Manhattan is wooed by a young painter, who also happens to be the son of her psychoanalyst.

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The Graduate (1967)

Plot Summary:

Benjamin, a recent college graduate is very worried about his future, he then finds himself in a love triangle with an older woman and her daughter.

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A Night in the Life of Jimmy Reardon (1988)

Plot Summary:

A recent high school graduate is faced with two options, either go to a business school where his father wants him to go to, or get a full time job. However he decides to defy his father and go to Hawaii. Trouble is he has no money. Along the way he comes to understand his parents and eventually bonds with his father.

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The Last Picture Show (1971)

Plot Summary:

The coming of age of a youth named Sonny in a small Texas town in the 1950s.

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Liberal Arts (2012)

Plot Summary:

Newly single, 35, and uninspired by his job, Jesse Fisher worries that his best days are behind him. But no matter how much he buries his head in a book, life keeps pulling Jesse back. When his favorite college professor invites him to campus to speak at his retirement dinner, Jesse jumps at the chance. He is prepared for the nostalgia of the dining halls and dorm rooms, the parties and poetry seminars; what he doesn’t see coming is Zibby – a beautiful, precocious, classical-music-loving sophomore. Zibby awakens scary, exciting, long-dormant feelings of possibility and connection that Jesse thought he had buried forever.

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Rushmore (1998)

Plot Summary:

When a beautiful first-grade teacher arrives at a prep school, she soon attracts the attention of an ambitious teenager named Max, who quickly falls in love with her. Max turns to the father of two of his schoolmates for advice on how to woo the teacher. However, the situation soon gets complicated when Max's new friend becomes involved with her, setting the two pals against one another in a war for her attention.

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Something's Gotta Give (2003)

Plot Summary:

Harry Sanborn is an aged music industry exec with a fondness for younger women like Marin, his latest trophy girlfriend. Things get a little awkward when Harry suffers a heart attack at the home of Marin's mother, Erica. Left in the care of Erica and his doctor, a love triangle starts to take shape.

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The Second Best Exotic Marigold Hotel (2015)

Plot Summary:

As the Best Exotic Marigold Hotel has only a single remaining vacancy - posing a rooming predicament for two fresh arrivals - Sonny pursues his expansionist dream of opening a second hotel.

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The Best Exotic Marigold Hotel (2011)

Plot Summary:

British retirees travel to India to take up residence in what they believe is a newly restored hotel. Less luxurious than its advertisements, the Marigold Hotel nevertheless slowly begins to charm in unexpected ways as the residents find new purpose in their old age.

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Under the Tuscan Sun (2003)

Plot Summary:

After a rough divoce, Frances, a 35 year old book editor from San Francisco takes a tour of Tuscany at the urgings of her friends. On a whim she buys Bramasole, a run down villa in the Tuscan countryside and begins to piece her life together starting with the villa and finds that life sometimes has unexpected ways of giving her everything she wanted.