10 Nostalgic Romantic Comedies From The 2000s That Will Take You Down Memory Lane

When the feeling that romance is dead starts to creep in, it’s time to turn to the nostalgic romantic-comedies from the 2000s to prove otherwise. The 2000s might have not been an amazing era for red carpet looks, but the romantic-comedies from this time period continue to shine through even today. In fact, movie fans often can’t help but hail the 2000s for the many rom-coms that would soon become instant classics following their release.

From the upbeat quirkiness of She’s the Man to the hilarious light-heartedness of Legally Blonde, 2000s romantic-comedies are a perfect mix of comedy gold and nostalgia that make the hearts of movie watchers everywhere flutter. Given that the 2000s were now over two decades ago, it’s finally the perfect time to reminisce about which of these rom-coms are must-watch films of the era. So, here are 10 of the best romantic-comedies for eager movie fans yearning for a charming and delightful blast back to the 2000s.

1. 13 Going on 30

Credit: Sony Pictures Releasing

  • Released: 2004
  • Directed by: Gary Winick

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.

2. How to Lose a Guy in 10 Days

Credit: Paramount Pictures

  • Released: 2003
  • Directed by: Donald Petrie

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.

3. She’s the Man

Credit: DreamWorks Pictures

  • Released: 2006
  • Directed by: Andy Fickman

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.

4. The Proposal

Credit: Walt Disney Studios Motion Pictures

  • Released: 2009
  • Directed by: Anne Fletcher

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.

5. Legally Blonde

Credit: MGM

  • Released: 2001
  • Directed by: Robert Luketic

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.

6. The Princess Diaries

Credit: Walt Disney Studios Motion Pictures

  • Released: 2001
  • Directed by: Garry Marshall

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.

7. Miss Congeniality

Credit: Warner Bros. Pictures

  • Released: 2000
  • Directed by: Donald Petrie

Miss Congeniality showcases Sandra Bullock’s knack for transforming unique characters into relatable personas: talent visible through her portrayal of Gracie Hart – a tomboyish FBI agent assigned to go undercover in a beauty pageant. Expertly led by director Donald Petrie, the movie offers rib-tickling humor and a sizzling dynamic between Bullock and love interest Benjamin Bratt. It also features a memorable performance from Michael Caine as Gracie’s pageant coach, propelling the film to cult status in the rom-com repertoire.

8. Enchanted

Credit: Walt Disney Studios Motion Pictures

  • Released: 2007
  • Directed by: Kevin Lima

Enchanted is Disney’s delightful blend of live-action and animation starring Amy Adams as Giselle – a naïve princess who falls victim to dastardly magic pushing her into reality’s harsh world where she encounters NYC lawyer Robert Philip (Patrick Dempsey). Through David Lima’s direction, viewers witness post-modern spin on fairy tales weaving together elements of romance, comedy, and musical genres. Fueled by stellar performances from the ensemble cast, including James Marsden and Susan Sarandon, Enchanted is a joyful experience that earned three Academy Award nominations for Best Original Song.

9. 50 First Dates

Credit: Sony Pictures Releasing

  • Released: 2004
  • Directed by: Peter Segal

50 First Dates pairs Adam Sandler with Drew Barrymore in this unique romantic comedy set in Hawaii as they meet during unusual circumstances. Directed by Peter Segal, the film chronicles Sandler’s character Henry Roth pursuing repetitive courtship due to Barrymore’s Lucy Whitmore suffering from short-term memory loss. With a subtle exploration of disability and commitment at its core, 50 First Dates established itself as a heartfelt rom-com full of innovative storytelling devices punctuated by captivating scenic backdrops.

10. Bridget Jones’s Diary

Credit: Universal Pictures

  • Released: 2001
  • Directed by: Sharon Maguire

Bridget Jones’s Diary explores Renee Zellweger’s transformation into Helen Fielding’s beloved titular character facing life choices while being caught up between two prospective suitors: her dashing boss (played by Hugh Grant) and standoffish childhood friend (portrayed by Colin Firth). Sharon Maguire brilliantly recreates London on-screen with humor-spirited dialogue while traversing themes such as body image stigma fulfillment challenges faced amid late-stage singledom;The movie received accolades throughout Hollywood, proving itself a consummate 2000s-era rom-com.