This curated list of films delves into the intriguing dynamics of workplace romance, focusing on relationships between bosses and their employees. These stories not only entertain but also explore themes of power, love, and the complexities of office politics, making them a fascinating watch for anyone interested in romantic narratives set in professional environments.

Working Girl (1988)
Description: Tess McGill, a secretary with big dreams, seizes an opportunity when her boss breaks her leg. She impersonates her boss to pitch an idea, leading to a romantic entanglement with a business executive.
Fact: Melanie Griffith won a Golden Globe for Best Actress for her role. The film was nominated for six Academy Awards, including Best Picture.


Sabrina (1995)
Description: Sabrina, the daughter of the Larrabee family's chauffeur, returns from Paris transformed and catches the eye of both Larrabee brothers, including her boss David. This remake explores the classic tale of unrequited love and social class.
Fact: This is a remake of the 1954 film starring Audrey Hepburn. Harrison Ford, known for action roles, took on a romantic lead here, showcasing his versatility.


How to Lose a Guy in 10 Days (2003)
Description: Andie Anderson, a magazine writer, tries to make Benjamin Barry, an advertising executive, dump her in 10 days for an article, while he bets he can make any woman fall in love with him in the same timeframe.
Fact: The film was based on a book of the same name by Michele Alexander and Jeannie Long. Kate Hudson and Matthew McConaughey had great on-screen chemistry.


Maid in Manhattan (2002)
Description: Marisa Ventura, a hotel maid, is mistaken for a wealthy socialite by a senatorial candidate, leading to a romantic entanglement where class differences and professional boundaries are tested.
Fact: Jennifer Lopez's character was inspired by a real-life incident involving a hotel maid. The film was a commercial success, grossing over $154 million worldwide.


Two Weeks Notice (2002)
Description: Lucy Kelson, a lawyer, resigns from her job as the chief counsel to George Wade, a charming but irresponsible real estate tycoon, leading to a romantic entanglement as they navigate their professional and personal lives.
Fact: Hugh Grant and Sandra Bullock had previously worked together in "Notting Hill." The film was a commercial success, grossing over $199 million worldwide.


Love Actually (2003)
Description: One of the many storylines involves Sarah, a graphic designer, who has feelings for her boss, Karl, showcasing the complexities of workplace romance amidst other intertwining love stories.
Fact: The film features an ensemble cast with many interconnected stories. It has become a holiday classic, often watched annually.


The Holiday (2006)
Description: While not directly about a boss-employee relationship, Amanda, a movie trailer editor, swaps homes with Iris, a journalist, leading to romantic encounters with their respective neighbors, showcasing the theme of unexpected love in professional settings.
Fact: The film was shot in both England and California, highlighting the contrast between the two settings. It was one of the highest-grossing romantic comedies of


The Devil Wears Prada (2006)
Description: While not a traditional romance, the dynamic between Miranda Priestly and her assistant Andy showcases a complex relationship where professional admiration turns into a form of respect and understanding, hinting at deeper feelings.
Fact: Meryl Streep's portrayal of Miranda Priestly was inspired by Vogue editor Anna Wintour. Streep won a Golden Globe for Best Actress for this role.


The Proposal (2009)
Description: Margaret, a high-powered book editor, faces deportation to Canada and convinces her assistant Andrew to marry her to stay in the U.S. Their fake engagement turns into real feelings, showcasing the classic boss-employee romance.
Fact: Sandra Bullock and Ryan Reynolds had great chemistry, leading to rumors of a real-life romance. The film was a box office hit, grossing over $317 million worldwide.


The Intern (2015)
Description: Ben Whittaker, a 70-year-old widower, becomes an intern at an online fashion site run by Jules Ostin. Their professional relationship blossoms into a deep friendship with hints of romance.
Fact: Robert De Niro and Anne Hathaway had to learn to ride bikes for the film. The movie was praised for its depiction of intergenerational friendship.
