The Best Romantic Comedies Of The 2000s, Ranked By Fans

How to Lose a Guy in 10 Days delivers an amusing war-of-the-sexes battle stacked with irresistible chemistry between leads - Kate Hudson and Matthew McConaughey. Directed by Donald Petrie, it revolves around Andie Anderson (Hudson), a journalist tasked with writing an article about driving away men using various tactics. She chooses advertising executive Benjamin Barry (McConaughey), unknowing that he has wagered his own bet involving dating women. This light-hearted romantic comedy captured audiences with its wacky premise while showcasing poignant insights into relationships.
 

She’s the Man is a delightful modern retelling of William Shakespeare’s “Twelfth Night”, pulling in Amanda Bynes' comic genius as Viola Hastings – disguised as her twin brother at boarding school. Joining forces with Channing Tatum in his breakout role, they engage in entertaining onscreen banter under Andy Fickman's direction. This rom-com delves into themes revolving around gender roles and identity while providing comedic moments and captivating performances from emerging talents like Alex Breckenridge.
 

In 13 Going on 30, Jennifer Garner masterfully plays Jenna Rink – an adolescent who wishes to grow up overnight but grapples with the ramifications of her life choices. Mark Ruffalo stars opposite as the supportive best friend Matt, lending his charm and down-to-earth demeanor to counterbalance Jenna's chaotic journey. Directed by Gary Winick, this touching fantasy-comedy reminds viewers about the importance of authentic connections while aging gracefully.
 

Legally Blonde turned Reese Witherspoon into America’s sweetheart when she portrayed sorority queen Elle Woods seeking justice by storming Harvard Law School after being dumped by her boyfriend Warner Huntington III (Matthew Davis). Director Robert Luketic successfully created an empowering story of self-discovery that challenges stereotypes about beauty versus intellect. The film's legacy includes a successful musical adaptation on Broadway and a much-awaited upcoming third installment, proving that persistence pays off.
 

The Princess Diaries catapulted Anne Hathaway into stardom as she starred alongside Julie Andrews in this charming Cinderella-esque tale directed by Garry Marshall. Based on Meg Cabot's best-selling novel series, the story follows a nerdy high school girl named Mia Thermopolis who discovers she is heir apparent to the Genovian throne. Showcasing themes of empowerment and acceptance amidst royal responsibilities and societal expectations, The Princess Diaries was nominated for numerous awards — earning recognition for supporting performances from Heather Matarazzo and Hector Elizondo.
 

The Proposal provides a delightful take on the classic fake relationship trope with two powerhouse actors, Sandra Bullock and Ryan Reynolds, leading the charge. The film follows a Canadian executive who convinces her overworked assistant to marry her in order to avoid deportation. Directed by Anne Fletcher, this sophisticated comedy deftly explores themes of power dynamics, vulnerability, and love in unexpected places. It received praise for sharp dialogue and contributed memorable moments to pop culture, like Bullock's dance scene with Betty White.