Top 10 Office Romance Comedies to Watch

Top 10 Office Romance Comedies to Watch Situation-Specific Comedies

Office romances have always been a rich vein for comedy, providing a backdrop where professional boundaries blur with personal feelings, often leading to hilarious situations. This collection of 10 films showcases the lighter side of workplace relationships, offering viewers not just laughter but also insights into the complexities of love in a professional setting. Whether it's the awkwardness of initial flirtations or the chaos of secret affairs, these films capture the essence of office romance with wit and charm.

Clue (1985)
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Clue (1985)

Description: Although primarily a mystery comedy, the film includes a humorous subplot involving a maid and a butler, highlighting the comedic potential of workplace relationships.

Fact: The film was based on the board game "Cluedo" and had three different endings.

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Office Space (1999)
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Office Space (1999)

Description: Peter Gibbons, an office worker, decides to rebel against his mundane job, leading to a series of comedic events including a romantic subplot with his colleague Joanna.

Fact: The character of Milton was inspired by an actual employee at Mike Judge's former office job.

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Love Actually (2003)
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Love Actually (2003)

Description: This ensemble film includes a storyline where a writer falls for his Portuguese housekeeper, showcasing the humor and awkwardness of workplace romance.

Fact: The film features multiple interconnected stories, with the office romance being just one of them.

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The Devil Wears Prada (2006)
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The Devil Wears Prada (2006)

Description: While not strictly a romance, the film features a dynamic between a fashion magazine editor and her assistant, filled with comedic moments and underlying romantic tension.

Fact: Meryl Streep's character was inspired by Vogue editor Anna Wintour.

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What's Your Number? (2011)
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What's Your Number? (2011)

Description: Ally Darling, after reading an article, decides to revisit her past lovers to find "the one," including a former colleague, leading to comedic workplace encounters.

Fact: The film was based on the novel "20 Times a Lady" by Karyn Bosnak.

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500 Days of Summer (2009)
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500 Days of Summer (2009)

Description: Tom Hansen, a greeting card writer, falls for Summer Finn, his boss's assistant, leading to a non-linear exploration of their relationship with plenty of workplace humor.

Fact: The film was originally titled "A Summer Thing."

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The Proposal (2009)
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The Proposal (2009)

Description: Margaret, a Canadian executive, faces deportation and convinces her assistant Andrew to marry her. Their fake engagement turns into a real romance amidst comedic workplace scenarios.

Fact: Sandra Bullock and Ryan Reynolds improvised many of their scenes, adding to the film's natural humor.

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Horrible Bosses (2011)
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Horrible Bosses (2011)

Description: Three friends plot to kill their unbearable bosses, but their plans go awry, leading to humorous situations, including a romantic entanglement with one of the bosses.

Fact: The film was originally titled "Untitled Workplace Comedy."

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The Intern (2015)
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The Intern (2015)

Description: Ben Whittaker, a 70-year-old widower, becomes an intern at an online fashion site, where he forms a bond with the company's CEO, Jules Ostin, blending mentorship with a touch of romance.

Fact: Robert De Niro and Anne Hathaway had never worked together before this film.

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The Internship (2013)
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The Internship (2013)

Description: Two out-of-work salesmen land internships at Google, where they navigate the tech world's challenges and form romantic connections with their younger colleagues.

Fact: The film was shot on location at Google's headquarters.

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