
Awkward Comedy movies
Cringe-powered, character-based humor: misreads, social discomfort, odd sincerity, and painfully funny situations.

91. Junebug
Comedy Drama Family Drama Awkward Comedy2005•1h 46min
United States
Director: Phil Morrison
Vibe
On the way to meet with an independent artist in the South, newlywed art dealer Madeleine is convinced by her husband, George, that they should stop to meet his family in North Carolina. Madeleine's affluent lifestyle clashes with the family, but she befriends George's wide-eyed and pregnant sister-in-law, Ashley, who is nearing her due date. Through the family, Madeleine gains greater insight into George's character.
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93. Pieces of April
Comedy Drama Family Drama Awkward Comedy2003•1h 21min
United States
Director: Peter Hedges
Vibe
Quirky and rebellious April Burns lives with her boyfriend in a low-rent New York City apartment miles away from her emotionally distant family. But when she discovers that her mother has a fatal form of breast cancer, she invites the clan to her place for Thanksgiving. While her father struggles to drive her family into the city, April -- an inexperienced cook -- runs into kitchen trouble and must ask a neighbor for help.
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94. About a Boy
Drama Comedy Romance Romantic Comedy Awkward Comedy2002•1h 41min
United Kingdom, United States
Director: Paul Weitz
Vibe
Will Freeman is a good-looking, smooth-talking bachelor whose primary goal in life is avoiding any kind of responsibility. But when he invents an imaginary son in order to meet attractive single moms, Will gets a hilarious lesson about life from a bright, but hopelessly geeky 12-year-old named Marcus. Now, as Will struggles to teach Marcus the art of being cool, Marcus teaches Will that you're never too old to grow up.
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95. Palindromes
Comedy Drama Coming-of-Age Drama Awkward Comedy2005•1h 40min
United States
Director: Todd Solondz
Vibe
Aviva is thirteen, awkward and sensitive. Her mother Joyce is warm and loving, as is her father, Steve, a regular guy who does have a fierce temper from time to time. The film revolves around her family, friends and neighbors.
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96. Hitch
Comedy Drama Romance Romantic Comedy Relationship Drama2005•1h 58min
United States
Director: Andy Tennant
Vibe
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.
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97. The Taste of Others
Drama Comedy Romance Romantic Comedy Awkward Comedy2000•1h 52min
France
Director: Agnès Jaoui
Vibe
Unpolished and ultra-pragmatic industrialist Jean-Jacques Castella reluctantly attends Racine's tragedy "Berenice" in order to see his niece play a bit part. He is taken with the play's strangely familiar-looking leading lady Clara Devaux. During the course of the show, Castella soon remembers that he once hired and then promptly fired the actress as an English language tutor. He immediately goes out and signs up for language lessons. Thinking that he is nothing but an ill-tempered philistine with bad taste, Clara rejects him until Castella charms her off her feet.
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98. Thumbsucker
Comedy Drama Coming-of-Age Drama Awkward Comedy2005•1h 36min
United States
Director: Mike Mills
Vibe
Justin Cobb, a teenager in suburban Oregon, copes with his thumb-sucking problem, romance, and his diagnosis with ADHD and subsequent experience using Ritalin.
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99. Notting Hill
Romance Comedy Romantic Comedy Awkward Comedy1999•2h 4min
United Kingdom, United States
Director: Roger Michell
Vibe
The life of William, the owner of a small bookshop in London, changes dramatically after a famous movie star visits his store. From there, the already unusual encounter grows into a romance.
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100. Something's Gotta Give
Drama Comedy Romance Romantic Comedy Awkward Comedy2003•2h 8min
United States
Director: Nancy Meyers
Vibe
When perpetually single, aging music industry exec Harry Sanborn, and his latest trophy girlfriend, Marin, arrive at her mother's beach house in the Hamptons, they find that her mother, playwright Erica Barry, also plans to stay for the weekend. Erica is scandalized by the relationship and Harry's sexist ways. But when Harry has a heart attack while there, and the doctor prescribes bedrest, his only option is to stay at the Barry home. Left in the care of Erica and his doctor, a love triangle starts to take shape.
