Dive into the world where love and business collide with our curated list of 10 romance films about entrepreneurship. These movies not only showcase the trials and tribulations of starting and running a business but also highlight the personal growth and romantic entanglements that come with it. Whether you're an aspiring entrepreneur or simply a fan of heartfelt stories, this collection offers a unique blend of inspiration and romance.

Working Girl (1988)
Description: A Staten Island secretary dreams of climbing the corporate ladder, but when her boss steals her idea, she must navigate the world of high finance to reclaim her success and find love along the way.
Fact: The film won an Academy Award for Best Original Song for Carly Simon's "Let the River Run."


You've Got Mail (1998)
Description: Two business rivals, who unknowingly fall in love through anonymous email exchanges, navigate the complexities of running competing bookstores and their budding romance.
Fact: The film was a modern retelling of the 1940 classic "The Shop Around the Corner."


Maid in Manhattan (2002)
Description: A hotel maid is mistaken for a wealthy guest, leading to a whirlwind romance with a senatorial candidate, highlighting themes of class, ambition, and personal identity.
Fact: Jennifer Lopez's character was inspired by a real-life story of a maid who was mistaken for a guest at a hotel.


Sweet Home Alabama (2002)
Description: A successful fashion designer returns to her small-town roots to finalize her divorce, only to find herself torn between her past and her entrepreneurial future in New York.
Fact: The film's title is a nod to the famous Lynyrd Skynyrd song, which is also featured in the movie.


The Holiday (2006)
Description: Two women, one a Hollywood movie trailer editor and the other a British journalist, swap homes for the holidays, leading to new business opportunities and romantic encounters.
Fact: The film's director, Nancy Meyers, also wrote the screenplay, known for her romantic comedies with strong female leads.


The Devil Wears Prada (2006)
Description: This film follows the journey of a young aspiring journalist who lands a job at a high-fashion magazine, exploring themes of ambition, personal growth, and the sacrifices required to succeed in the cutthroat world of fashion.
Fact: The film was based on a novel by Lauren Weisberger, who drew inspiration from her own experiences working as an assistant to Vogue editor-in-chief Anna Wintour.


The Proposal (2009)
Description: A high-powered book editor faces deportation and convinces her assistant to marry her to stay in the country, leading to unexpected business and romantic developments.
Fact: The film was shot in Alaska, where the fictional town of Sitka was created for the movie.


The Ugly Truth (2009)
Description: A TV producer and a chauvinistic correspondent clash over their views on love, leading to a bet that intertwines their professional and personal lives in unexpected ways.
Fact: The film was one of the first major roles for Katherine Heigl after her success on "Grey's Anatomy."


Crazy, Stupid, Love (2011)
Description: After his wife leaves him, a recently divorced man tries to reinvent himself in the dating world, while his son navigates his own entrepreneurial endeavors and romantic life.
Fact: The film was originally titled "Untitled Marital Crisis Project" during its development.


The Intern (2015)
Description: A retired widower becomes an intern at an online fashion site, where he forms an unlikely friendship with the company's workaholic CEO, exploring themes of mentorship, entrepreneurship, and personal connection.
Fact: Robert De Niro, who plays the intern, was actually 71 years old during filming, making his character's age quite accurate.
