Romance, laughter, and the quirky twists of fate – the 2000s were a treasure trove of rom-coms that, while not all blockbusters, captured our hearts in unique ways. Here are just some of them:
1. Happy Accidents (2000)
Rotten Tomatoes score: 70%
In this romantic comedy, a young woman from New York falls in love with a quirky man who claims to be a time traveler from the year 2470, leading to a blend of romance and skepticism.
2. Love & Sex (2000)
Rotten Tomatoes score: 47%
This film explores the romantic journey of a magazine writer who, after a series of failed relationships, recounts her love life to understand her current relationship's complexities and the meaning of true love.
3. Waking Life (2001)
Rotten Tomatoes score: 81%
An animated drama featuring a young man trapped in a continuous loop of lucid dreams, exploring philosophical concepts through a series of eclectic encounters and conversations.
4. Kissing Jessica Stein (2001)
Rotten Tomatoes score: 83%
A romantic comedy-drama about a woman, Jessica Stein, who, frustrated with her unsuccessful love life with men, finds herself in a romantic relationship with a woman, challenging her perceptions and societal norms.
5. Sidewalks of New York (2001)
Rotten Tomatoes score: 56%
A seriocomic tale that interweaves the lives and loves of six New Yorkers, exploring their romantic and sexual entanglements, and how their paths cross in unexpected ways.
6. Tadpole (2002)
Rotten Tomatoes score: 77%
A coming-of-age comedy where a 15-year-old boy, infatuated with his stepmother, experiences a series of humorous and awkward encounters during his Thanksgiving break in New York.
7. The Good Girl (2002)
Rotten Tomatoes score: 82%
The story of a disenchanted retail worker whose mundane life takes a turn when she begins an affair with a younger co-worker, bringing unforeseen consequences.
8. Pieces of April (2003)
Rotten Tomatoes score: 84%
A heartwarming comedy-drama about April, a rebellious young woman who attempts to host a Thanksgiving dinner for her estranged family in her tiny New York City apartment, facing various challenges along the way.
9. The Baxter (2005)
Rotten Tomatoes score: 32%
In this romantic comedy, a conservative and awkward accountant, known for always being the 'baxter' (the safe but unexciting choice), faces the ultimate challenge when his fiancée's old flame reappears before their wedding.
10. Trust the Man (2005)
Rotten Tomatoes score: 29%
This film portrays the romantic and sexual challenges of two New York couples, delving into themes of fidelity, love, and relationship struggles.
11. Lars and the Real Girl (2007)
Rotten Tomatoes score: 81%
An endearing tale of a socially awkward man who develops a non-traditional relationship with a life-size doll, leading his entire community to embrace the situation in unexpected ways.
12. Waitress (2007)
Rotten Tomatoes score: 89%
A charming tale of a small-town waitress, expert pie maker, and in an unhappy marriage, who sees a pie contest and a new doctor in town as her chance for a fresh start.
13. Chasing Liberty (2004)
Rotten Tomatoes score: 18%
This romantic comedy follows the President's daughter who, craving freedom from her highly public life, escapes her Secret Service detail on a European adventure, finding love and adventure along the way.
14. The Nanny Diaries (2007)
Rotten Tomatoes score: 34%
A comedy-drama about a college graduate working as a nanny for a wealthy and dysfunctional Manhattan family, providing an inside look at the upper class's lifestyle and parenting.
15. Penelope (2006)
Rotten Tomatoes score: 53%
This modern fairy tale centers on Penelope, a young woman cursed with a pig's snout for a nose, who embarks on a journey of self-discovery and finds love in an unexpected place.
16. The Accidental Husband (2008)
Rotten Tomatoes score: 6%
A romantic comedy where a love advice radio host finds her own life turned upside down when she unwittingly causes a listener's engagement to end, leading to unexpected romantic entanglements.
17. Definitely, Maybe (2008)
Rotten Tomatoes score: 71%
In this romantic drama, a father narrates his past romantic relationships to his daughter, leading her to guess who her mother is among his past loves.
18. Miss Pettigrew Lives for a Day (2008)
Rotten Tomatoes score: 78%
Set in pre-WWII London, this film tells the story of a middle-aged governess who becomes the social secretary of a young actress and is introduced to a glamorous and exhilarating lifestyle, challenging her traditional values.
19. Management (2008)
Rotten Tomatoes score: 46%
A quirky romantic tale where a traveling saleswoman engages in a brief fling with an awkward motel manager, who then pursues her across the country, leading to unexpected love and self-discovery.
20. 500 Days of Summer (2009)
Rotten Tomatoes score: 85%
Starring Joseph Gordon-Levitt and Zoe Deschanel, this film chronicles the non-linear story of a hopeless romantic and his relationship with a woman who doesn't believe in true love; disillusioned, the main character is experiencing love, heartbreak, and finally the understanding that some things are not what they seem.
21. Away We Go (2009)
Rotten Tomatoes score: 67%
A pregnant couple travels across the U.S. to find the perfect place to start their family, encountering a variety of eccentric friends and relatives along the way, forcing them to confront their own ideals and aspirations.
22. Gigantic (2008)
Rotten Tomatoes score: 35%
The plot centers around a mattress salesman and a quirky woman he meets at his store, leading to an unusual relationship filled with unexpected twists, including the man's lifelong dream to adopt a Chinese baby.
23. I Love You, Beth Cooper (2009)
Rotten Tomatoes score: 13%
In this teen comedy, a nerdy valedictorian professes his love for the most popular girl in school during his graduation speech, leading to a wild night of adventure and self-discovery.
24. The Marc Pease Experience (2009)
Rotten Tomatoes score: 18%
A man stuck reliving his high school glory days as a star performer in musicals struggles to come to terms with his past and present, culminating in a humorous yet poignant journey of self-realization.
25. My Life in Ruins (2009)
Rotten Tomatoes score: 10%
A romantic comedy about a disillusioned tour guide in Greece who rediscovers her romantic side and zest for life as she leads a group of eccentric tourists.
26. Post Grad (2009)
Rotten Tomatoes score: 8%
This film follows a recent college graduate struggling to navigate the unpredictable world of adulthood and career, while also dealing with her complicated love life and eccentric family.
27. Spread (2009)
Rotten Tomatoes score: 22%
A comedy-drama centering on a serial womanizer and his lifestyle in Los Angeles, which is upended when he meets a woman who challenges his ways, leading to unexpected feelings and choices.
28. The Brothers Bloom (2008)
Rotten Tomatoes score: 68%
In this adventure comedy, two con artist brothers decide to pull off one final grand scam on a quirky heiress, only to find their personal lives complicated by real emotions.
29. Youth in Revolt (2009)
Rotten Tomatoes score: 67%
A coming-of-age story where a teenager adopts a rebellious alter ego in an attempt to win over his dream girl, leading to a series of comic misadventures and a journey of self-discovery.