Most Similar Movies to Sideways (2004)
If you are looking for movies like Sideways (2004), you might like movies tagged with keyword : writer, actor, waitress, server, wife, amusing, endearing, playful, emotional, san diego, friendship, midlife crisis, male bonding, affair, road trip, adventure, temptation, growing up, 2000s .
My Best Friend's Wedding (1997), When Harry Met Sally... (1989), Love, Rosie (2014), Made of Honor (2008), Love Me If You Dare (2003), Aquamarine (2006), Sleeping with Other People (2015) ... Let's take a look at the following list...

My Best Friend's Wedding (1997)
When a woman's long-time friend reveals he's engaged, she realizes she loves him herself and sets out to get him, with only days before the wedding.
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When Harry Met Sally... (1989)
Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship.
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Love, Rosie (2014)
Rosie and Alex have been best friends since they were 5, so they couldn't possibly be right for one another...or could they? When it comes to love, life and making the right choices, these two are their own worst enemies.
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Made of Honor (2008)
A guy in love with an engaged woman tries to win her over after she asks him to be her maid of honor.
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Love Me If You Dare (2003)
As adults, best friends Julien and Sophie continue the odd game they started as children -- a fearless competition to outdo one another with daring and outrageous stunts. While they often act out to relieve one another's pain, their game might be a way to avoid the fact that they are truly meant for one another.
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Aquamarine (2006)
Two teenage girls discover a mermaid in their beach club's swimming pool.
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Sleeping with Other People (2015)
A good-natured womanizer and a serial cheater form a platonic relationship that helps reform them in ways, while a mutual attraction sets in.
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The Sisterhood of the Traveling Pants 2 (2008)
Four college freshmen and best friends find that it may take more than a shared pair of jeans to help them stay in touch as their lives go in different directions.
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Friends with Kids (2011)
Two best friends decide to have a child together while keeping their relationship platonic, so they can avoid the toll kids can take on romantic relationships.
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Lage Raho Munna Bhai (2006)
Munna Bhai embarks on a journey with Mahatma Gandhi in order to fight against a corrupt property dealer.
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Manhattan (1979)
The life of a divorced television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.
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Beautiful Girls (1996)
A piano player at a crossroads in his life returns home to his friends and their own problems with life and love.
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200 Cigarettes (1999)
A collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses.
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Something Borrowed (2011)
Friendships are tested and secrets come to the surface when terminally single Rachel falls for Dex, her best friend Darcy's fiancé.
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Bridesmaids (2011)
Competition between the maid of honor and a bridesmaid, over who is the bride's best friend, threatens to upend the life of an out-of-work pastry chef.
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Husbands and Wives (1992)
When their best friends announce that they're separating, a professor and his wife discover the faults in their own marriage.
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The Intouchables (2011)
After he becomes a quadriplegic from a paragliding accident, an aristocrat hires a young man from the projects to be his caregiver.
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Bride Wars (2009)
Two best friends become rivals when they schedule their respective weddings on the same day.
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