Best movies like The Truth About Jane and Sam

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Not Cool (2014)

Plot Summary:

NOT COOL follows former prom king and college freshman Scott (Shane Dawson) who has just returned home for Thanksgiving break only to be dumped by his eccentric, long-term girlfriend. With his world turned upside down, Scott strikes an unlikely friendship with former classmate Tori (Cherami Leigh), an ugly duckling who blossomed in her first semester of college. Together, the two embark on an outrageous adventure through their hometown. But when Scott and Tori find their friendship turning into something deeper, they realize that a few months away may have changed them more than they realized.

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Dish Dogs (2000)

Plot Summary:

Two friends travel from town to town taking jobs as dishwashers until they both find love and must choose separate paths.

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AV (2005)

Plot Summary:

The story of four soon-to-be-college grads who are about to embark on the big adventure known as life. The foursome concoct an elaborate plan to hire a Japanese porn actress (or "AV Girl") for a fake film. Then they'll have sex with her. What could go wrong?.

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Love in a Puff (2010)

Plot Summary:

Jimmy is a mild mannered advertising executive in his twenties. While smoking in an alley packed with booming loudmouth co-workers and sharing explicit gossips and horror stories, he befriends a misfit cosmetics salesgirl Cherie who also likes to light up. An awkward romance soon blossoms amidst the anxiety of their nicotine rush. As they become more attached to each other, they also find themselves moving farther away from their regular hot pot pack into their own private alley, where their conversations suggest more emotional depths, covering the collision of reality and delightfully trivial matters of the bizarre people around them.

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Easy! (2011)

Plot Summary:

Bruno Beltrame makes a living of sorts. He wanted to be a great writer but he is content to write the books of others. He also gives private lessons to students who are not serious. Among his pupils is fifteen-year-old Luca, more quick-witted and revolted than the others. The day he meets his mother, a woman he once loved, Luca gets upset when she tells him bluntly that not only Luca is his son but that she intends to entrust him to his care as well.

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Love on the Rocks (2004)

Plot Summary:

Wong is shocked to learn from his girlfriend Annie (Leung) that she wants to break up. He decides to go online and seek help from love experts on the net. He finds Crystal, a 19-year old self-proclaimed love advisor who has never been actually involved in a relationship. As she assists Wong by telling him to revisit all of his ex-girlfriends in order to find out the root of his problems, the two of them also find themselves falling for one another.

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To All the Boys: P.S. I Still Love You (2020)

Plot Summary:

Lara Jean and Peter have just taken their romance from pretend to officially real when another recipient of one of her love letters enters the picture.

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Cheeky Girls (2008)

Plot Summary:

Three teen-aged girlfriends navigate multiple love triangles.

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The First Time (2012)

Plot Summary:

Dave, a high school senior, spends most of his time pining away over a girl he can’t have. Aubrey, a junior with artistic aspirations, has a hot boyfriend who doesn’t quite understand her or seem to care. Although they go to different schools, Dave and Aubrey find themselves at the same party. When both head outside to get some air, they meet. A casual conversation sparks an instant connection, and, over the course of a weekend, things turn magical, romantic, complicated, and funny as Aubrey and Dave discover what it's like to fall in love for the first time.