Most Similar Movies to Medicine for Melancholy (2008)
If you are looking for movies like Medicine for Melancholy (2008), you might like movies tagged with keyword : romance, drama, independent film, american film, urban life, race relations, african american, san francisco, social issues, cultural differences, identity, modern relationships, low budget film, black and white photography, art film, urban romance, young couple, emotional exploration, social commentary, realistic theme .
Ray Meets Helen (2017), Breathe In (2013), Splendor (1999), Baby, Baby, Baby (2015), Me and You and Everyone We Know (2005), The Upside of Anger (2005), 1 Night (2016) ... Let's take a look at the following list...

Ray Meets Helen (2017)
In bizarre, unrelated turns of events, Ray and Helen each happen upon large sums of money which give them the chance to re-invent themselves.
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Breathe In (2013)
When a foreign exchange student arrives in a small upstate New York town, she challenges the dynamics of her host family's relationships and alters their lives forever.
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Splendor (1999)
Veronica, 22, meets a writer and a drummer hunk at a club on Halloween. Why choose when she can have both? 3some? But then a third man comes along.
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Baby, Baby, Baby (2015)
The relationship between two mismatched people who try to move past their baggage to make their love work.
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Me and You and Everyone We Know (2005)
A lonely shoe salesman and an eccentric performance artist struggle to connect in this unique take on contemporary life.
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The Upside of Anger (2005)
When her husband unexpectedly disappears, a sharp-witted suburban wife and her daughters juggle their mom's romantic dilemmas and family dynamics.
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1 Night (2016)
Past and present collide when an adult couple (Anna Camp, Justin Chatwin) and two teens explore love over the course of one night at a hotel.
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Someone, Somewhere (2019)
Rémy, a young Parisian with an unskilled job. Mélanie, a young she-Parisian who works in scientific research. Two depressive moods living in close proximity but strange to each other. Shall the two ever meet?
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Lovelife (1997)
Love triangles abound in this romantic comedy involving students and teachers at a graduate school. Aspiring writer Zoey (Saffron Burrows) and her boyfriend, Danny (Matthew Letscher), have a hot-and-cold relationship, which is put in jeopardy when Danny's longtime friend, Amy (Carla Gugino), professes her love for him. Zoey is also involved with a professor, Alan (Jon Tenney), who lives with the airheaded Molly (Sherilyn Fenn), who in turn has eyes for mature professor Bruce (Bruce Davison).
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Expired (2007)
A turbulent and intriguing love story between two parking officers in the city of Los Angeles.
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A French Gigolo (2008)
A married construction worker leads a double life as a male prostitute serving rich ladies.
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People You May Know (2017)
An introvert realizes he can be whomever he wants to be on the Internet.
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Middle of Nowhere (2012)
A med student (Emayatzy Corinealdi) considers leaving her long-imprisoned husband (Omari Hardwick) for a charming bus driver (David Oyelowo).
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Everyone Else (2009)
A Mediterranean vacation reveals cracks in a couple's relationship.
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Eloïse's Lover (2009)
A beautiful woman (Ariadna Cabrol) begins a lesbian affair with an 18-year-old high-school student (Diana Gómez).
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Non-Fiction (2018)
A controversial Parisian writer blurs the line between fact and fiction when he starts to use real-life love affairs as fodder for his explosive new novel.
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Mango Kiss (2003)
"Mango Kiss" is a story about Lou whose world turns upside-down when she falls in love with her best friend Sassafras. They journey to San Francisco and stumble into the wild world of role-playing and non-monogamous S/M dykes. Comedy ensues as these wholesome girls get in over their heads.
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3-Iron (2004)
A transient young man breaks into empty homes to partake of the vacationing residents' lives for a few days.
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