The Best 2000s Rom-Coms for a Feel-Good Movie Night

If you're looking for lighthearted love stories, look no further than these iconic rom-coms.
The Best 2000s Rom-Coms for a Feel-Good Movie Night
Photo: IMDb
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Brittany Barber
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Brittany Barber
The Knot Contributor
  • From top movie picks to celebrity scoops and travel advice, Brittany writes on a wide range of topics for The Knot.
  • While Brittany is a contributing writer for The Knot Worldwide, she also provides shopping content for publications like BuzzFeed, CTV and The National Post.
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Updated Oct 30, 2023
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From quirky meet-cutes to heartwarming declarations of love, 2000s rom coms delivered some of the most beloved love stories we continue to watch today. These films not only captured the essence of their time, but also continue to captivate audiences of all generations with laugh-out-loud storylines. From modern adaptations of Shakespeare to stories of bridesmaids, FBI agents and high schoolers, romantic movies from the 2000s offered something for everyone.

In this article, our editors will take you on a romantic trip down memory lane to revisit the absolute best rom-coms. We're talking about the iconic movies that defined the decade, like Miss Congeniality and 13 Going on 30. Whether you're seeking a feel-good watch or on the hunt for girl's night recommendations, we've got you covered. Get ready to laugh, cry and fall in love all over again as we dive into the most heartwarming, hilarious and nostalgic romance movies the 2000s had to offer.

The Knot's 2000s Rom Com Ranking

When it comes to 2000s rom coms, here are The Knot Editors' favorites.

Most Nostalgic: Princess Diaries

Funniest: Miss Congeniality

Best Musical: Mama Mia!

Most Underrated: Monsoon Wedding

Best Holiday Rom Com: The Holiday

Editor's Favorite: Hitch

Read on for all 29 of our favorite 2000s rom coms.

Love Actually

Best 2000s Rom Coms - Love Actually
Photo: IMDb

With a star-studded cast (we're talking Hugh Grant, Emma Thompson, Keira Knightley and Liam Neeson) this 2000s rom com weaves together several love stories set in the weeks leading up to Christmas in London.

Release Date: September 7, 2003 | Watch Trailer

Monsoon Wedding

Best 2000s Rom Coms - Monsoon Wedding
Photo: IMDb

The Verma family descends upon New Delhi for a reunion and a last-minute wedding. With five different stories of family members intersecting, love (especially familial love) shines through despite class, location and belief systems.

Release Date: February 22, 2002 | Watch Trailer

Bridget Jones's Diary

Best 2000s Rom Coms Bridget Jones's Diary movie poster
Photo: IMDb

This quirky 2000s rom com follows Bridget Jones (Renée Zellweger) on her whirlwind journey of self-discovery and love in this modern adaptation of Jane Austen's Pride and Prejudice.

Release Date: April 13, 2001 | Watch Trailer

500 Days of Summer

Best 2000s Rom Coms - 500 Days of Summer movie poster
Photo: Amazon

If you want a break from the usual conventions of romantic comedies, look no further than 500 Days of Summer. With a witty script and nonlinear narrative, this film depicts the highs and lows of Tom (Joseph Gordon-Levitt) and Summer's (Zooey Deschanel) 500-day-long love story.

Release Date: July 17, 2009 | Watch Trailer

The Proposal

Best 200s Rom Coms - The Proposal movie poster
Photo: IMDb

Sandra Bullock and Ryan Reynolds star in this hilarious romantic comedy about a Canadian executive who convinces her assistant to marry her in a fake engagement to avoid deportation. In true rom com fashion, their game of pretend sparks into something more — leading to all the feel-good moments we love to see in our favorite 2000s rom coms.

Release Date: June 19, 2009 | Watch Trailer

Sweet Home Alabama

In this early 2000s rom com, we meet Melanie (played by Reese Witherspoon), a New York fashion designer who returns to her Southern roots, revisiting her past and rekindling an old romance.

Release Date: September 27, 2002 | Watch Trailer

Mamma Mia!

Best 200s Rom Coms - Mamma Mia! Movie poster
Photo: Amazon

This lively musical is one of the best when it comes to feel good 2000s rom coms. Featuring everyone's favorite ABBA songs, the story follows the soon-to-wed Sophie (Amanda Seyfried), who desperately wants to meet her estranged father before the big day. The twist? She's not sure who her father is, so she invites three of her mother's ex-lovers to the wedding!

Release Date: July 18, 2008 | Watch Trailer


Best 200s Rom Com - Hitch
Photo: IMDb

Will Smith plays a professional dating consultant, Alex "Hitch" Hitchens, who helps awkward clients woo their crushes. Things get complicated when he falls for Sara (Eva Mendes), a gorgeous gossip columnist, who changes everything for him.

Release Date: February 11, 2005 | Watch Trailer

She's the Man

In this hilarious adaptation of Shakespeare's Twelfth Night, Amanda Bynes disguises herself as her brother to prove that her soccer skills are just as good as any boy's — entangling herself in a few complicated romances along the way.

Release Date: March 17, 2006 | Watch Trailer

How to Lose a Guy in 10 Days

Best 200s Rom Coms - How to Lose a Guy in 10 Days
Photo: IMDb

This classic 2000s rom com follows the misadventures of a magazine columnist (Kate Hudson) who tries to drive away her new boyfriend (Matthew McConaughey) as part of an assignment. Unknown to her, this new boyfriend of hers is actually on his own mission to make a woman fall in love with him.

Release Date: January 27, 2003 | Watch Trailer

13 Going on 30

Best 200s Rom Coms - 13 Going on 30 movie poster
Photo: Amazon

In this whimsical rom com, we meet a 13-year-old girl named Jenna, who, after making a wish to become 30, wakes up to find herself a successful and fashionable 30-year-old woman played by Jennifer Garner. She quickly learns that her life is not what she had hoped it would be and sets out to try to fix it.

Release Date: April 23, 2004 | Watch Trailer

Miss Congeniality

In a classic fish-out-of-water scenario, the clumsy Gracie (played by Sandra Bullock) is thrown into a beauty pageant as an undercover agent to prevent a terrorist threat. With plenty of hilarious and heartwarming moments, she navigates this unfamiliar world — and discovers romance along the way.

Release Date: December 14, 2000 | Watch Trailer

Legally Blonde

In this timeless 2000s classic, we meet the charismatic Elle Woods (Reese Witherspoon), a fashionable, blonde sorority girl who's a heck of a lot smarter than the people around her give her credit for. When she gets into Harvard Law School to win back her ex-boyfriend, she discovers her own potential and finds the love she actually deserves.

Release Date: October 11, 2001 | Watch Trailer

Ella Enchanted

This whimsical fantasy film is set in a magical world where a young girl named Ella (Anne Hathaway) is burdened with the curse of obedience. She embarks on a quest to break this spell, encountering a charming prince, wicked stepsisters and all sorts of mythical creatures along the way.

Release Date: April 9, 2004 | Watch Trailer

My Big Fat Greek Wedding

Best 200s Rom Coms - My Big Fat Greek Wedding Movie Poster
Photo: IMDb

This romantic comedy tells the story of Toula (Nia Vardalos), a Greek-American woman, as she navigates her family's traditional Greek values while falling for a non-Greek man named Ian (John Corbett).

Release Date: August 16, 2002 | Watch Trailer

27 Dresses

In this 2000s rom com, we follow the story of Jane (Katherine Heigl), who is always a bridesmaid but never a bride. As she navigates an unrequited romance, a complicated situation with her sister and potential new love interest, this film is full of funny and relatable moments that still resonate with viewers today.

Release Date: January 9, 2008 | Watch Trailer

Along Came Polly

Best 200s Rom Coms - Along Came Polly
Photo: IMDb

Starring Jennifer Aniston and Ben Stiller, this rom com follows the misadventures of Reuben (Stiller), a risk-averse insurance analyst, whose new bride cheats on him during their honeymoon. Eventually, Reuben finds solace and unexpected love when he meets the free-spirited and carefree Polly (Aniston).

Release Date: January 16, 2004 | Watch Trailer

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The Holiday

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Direction: please pull the poster

When it comes to 2000s rom coms to watch over the holidays, it doesn't get much better than The Holiday starring Cameron Diaz, Kate Winslet, Jude Law and Jack Black. The story follows two women who swap homes over the holidays and fall in love along the way.

Release Date: December 8, 2006 | Watch Trailer

Two Weeks Notice

Sandra Bullock and Hugh Grant star in this workplace rom com about an attorney named Lucy and her charming but demanding boss. When Lucy quits her position, their professional relationship becomes increasingly personal — leading to a romance neither of them expected.

Release Date: December 12, 2002 | Watch Trailer

Win a Date with Tad Hamilton!

In this underrated 2000s rom com, we meet Rosalee (Kate Bosworth), a small-town grocery store cashier, who wins a date with the famous actor Tad Hamilton (Josh Duhamel). When the date goes better than expected, a quirky love triangle forms when Rosalee's best guy friend (Topher Grace) becomes jealous.

Release Date: January 23, 2004 | Watch Trailer

The Princess Diaries

This classic 2000s movie follows Mia Thermopolis (Anne Hathaway), a teenage girl who discovers she's the heir to the throne of Genovia. As she learns the challenges of royal etiquette (and undergoes an epic makeover), she also juggles the ups and downs of teenage life — navigating friendships, popularity, crushes and romance.

Release Date: July 29, 2001 | Watch Trailer

Made of Honor

This 2000s romantic comedy tells the story of Tom (Patrick Dempsey), a man who realizes he's in love with his best friend Hannah (Michelle Monaghan) just when she announces her engagement to someone else.

Release Date: May 2, 2008 | Watch Trailer


Best 200s Rom Coms - Enchanted
Photo: IMDb

This romantic fantasy film playfully combines traditional Disney animation with live-action sequences. The story follows Giselle (Amy Adams), a fairytale princess who is transported to modern-day New York City. In order to break a spell, she must navigate the real world and find true love's kiss.

Release Date: November 21, 2007 | Watch Trailer

The Wedding Planner

Best 200s Rom Coms - The Wedding Planner movie poster
Photo: Amazon

The Wedding Planner is a classic 2000s rom com starring Jennifer Lopez as Mary, a successful wedding planner who doesn't have the best luck when it comes to finding love herself. When she meets a charming doctor (Matthew McConaughey), all kinds of misadventures unfold, including the realization that he's about to marry one of her clients.

Release Date: January 26, 2001 | Watch Trailer

Crazy, Stupid, Love

When it comes to hilarious romantic comedies, look no further than Crazy, Stupid, Love. When Cal (Steve Carell) faces sudden divorce and finds himself adrift in the world of dating, he gets advice from the charming Jacob (Ryan Gosling), which eventually leads to unexpected and hilarious romantic entanglements.

Release Date: July 29, 2011 | Watch Trailer

Just My Luck

This quintessential 2000s rom com follows the story of Ashley Albright (Lindsay Lohan), a young woman who seemingly has everything go her way due to her extraordinary luck. However, when she shares a kiss with an unlucky guy (Chris Pine), their fortunes switch, leading to all sorts of ridiculous moments.

Release Date: May 12, 2006 | Watch Trailer

50 First Dates

Best 200s Rom Coms - 50 First Dates
Photo: IMDb

In this heartwarming rom com, we meet Henry (Adam Sandler), who falls for a woman named Lucy (Drew Barrymore). The catch? Lucy has short-term memory loss and forgets each day's events when she goes to sleep, meaning Henry has to reintroduce himself to her over and over again in order to win her heart.

Release Date: February 13, 2004 | Watch Trailer

Just Like Heaven

This classic rom com follows the story of a lonely landscape architect (Mark Ruffalo) who moves into a new apartment, only to discover it's already inhabited by the spirit of its previous tenant (Reese Witherspoon). As the two form an unlikely bond, they embark on a charming and otherworldly journey to help her understand what happened to her.

Release Date: September 16, 2005 | Watch Trailer

The Prince & Me

In this royal rom com from the 2000s, we meet Paige (Julia Stiles), a pre-med college student, who unexpectedly falls in love with Edvard (Luke Mably), a charming prince from Denmark disguised as an ordinary student at her university.

Release Date: April 2, 2004 | Watch Trailer

Knocked Up

Best 200s Rom Coms - Knocked Up
Photo: IMDb

This raunchy and hilarious rom com follows Ben (Seth Rogen), a fun-loving slacker and Alison Scott (Katherine Heigl), an up-and-coming entertainment journalist, who have a one-night stand that results in an unexpected pregnancy.

Release Date: June 1, 2007 | Watch Trailer

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