15 Best Rom-Coms Of The 2000s, Ranked

The oldest recorded stories of the human race describe how we came to be. While they often include mythical figures and parables to teach us lessons on how to live our lives, these tales also touch on passion, devotion, and tenderness. Or, in a single word: Love. From Adam and Eve to Isis and Osiris to Layla and Manjun, every culture has volumes about the universal feeling of love. Whether we're talking about finding it, keeping it, or simply reveling in it, who doesn't love a good love story?

Though the mediums have evolved and expanded over the years, we still have plenty of love stories in modern culture. In terms of movies, many will flock to romantic comedies like "It Happened One Night," "When Harry Met Sally," or "To All the Boys I've Loved Before" to get their fix. And though every generation has its own favorites, many out there turn to the 2000s for some of the most memorable rom-coms of all time. To honor them, we've compiled a list of the 15 best offerings from the genre that were released between 2000 and 2009.

Much like Kevin Smith's "Chasing Amy," which touches on themes that are commonplace in modern times, "40 Days and 40 Nights" restarted a conversation about sex, intimacy, and relationships when it was released.

Josh Hartnett plays Matt Sullivan, a heartbroken web designer who is hung up on his ex-girlfriend and experiencing sexual dysfunction with other women because of it. After talking to his brother (a Catholic priest-in-training) about his issues, Matt decides to give up sexual contact for Lent. But once his colleagues find out, they set up an open-invite betting pool that says Matt will break his vow of abstinence before the end of the religious quarantine. He manages to resist the onslaught of temptation ... until things get harder (no pun intended) as he starts seeing Shannyn Sossamon's Erica, who knows nothing about Matt's sacrifice.

The climax (OK, pun intended) of the 2002 film is definitely a red flag since Matt's ex rapes him while he's asleep, but his relationship with Erica creatively shows how A) all genders can put sex on a pedestal and B) there are ways to be intimate with a partner beyond just having sex.

If any time of the year was to be considered rom-com season, Christmas time would be a strong contender. Throughout the 2000s, a number of films premiered that would go on to become December staples from that point forward. And while we can't cover all of them, our list includes three modern holiday classics, starting with "Love Actually."

Written and directed by eminent British romantic comedy filmmaker Richard Curtis, the 2003 movie showcases an all-star ensemble cast including Alan Rickman, Emma Thompson, Martin Freeman, Laura Linney, Bill Nighy, and more as they depict various aspects of love across 10 interconnected stories that take place in the weeks leading up to Christmas. Whether it's platonic, romantic, extravagant, unexpected, misguided, or even cringey (looking at you, Andrew Lincoln's Mark), as Hugh Grant's Prime Minister character says in the opening narration, "Love actually is all around," and it's all covered in this fan-favorite film.

"Pride and Prejudice" is one of the most beloved romance novels ever written, so there are plenty of adaptations from all over the world. When it comes to the 2000s, many fans might immediately recall the 2005 film starring Keira Knightley. However, that version definitely isn't a rom-com. Luckily, 2004's "Bride and Prejudice" exists to give fans of that genre their Jane Austen fix.

Following the success of "Bend It Like Beckham," filmmaker Gurinder Chadha took the classic tale and remixed it by blending a Bollywood musical with Hollywood flare. The film stars Aishwarya Rai as eligible bachelorette Lalita Bakshi, this version's Elizabeth. She crosses paths with the wealthy and handsome Will Darcy (played by Martin Henderson) at an arranged marriage ceremony. But despite Darcy's initial objections to the cultural traditions of Amritsar, India and Lalita's family coming to light, this globe-trotting love story still finds a way to bring these star-crossed lovers together in a fun and flamboyant film. The charismatic cast also includes Naveen Andrews, Indira Varma, and Alexis Bledel.

Not only did her character in "13 Going On 30" popularize the phrase, but Jennifer Garner truly embodied "30, flirty, and thriving" in the 2000s. After landing a series of small roles in various films, she became Sydney Bristow in J.J. Abrams' hit series "Alias." At the same time, thanks to Gary Winick's 2004 fantasy rom-com about a New Jersey teen who finds herself waking up the morning after her 13th birthday in her dream NYC adult life, the actress broke out in her first of many leading film roles.

Not only was Garner thrust into the spotlight due to her uninhibited and blissful performance as Jenna Rink, but co-star Mark Ruffalo emerged as a standout as well. His Matty, who was Jenna's childhood best friend and eventual dorky yet thoughtful love interest, helped to drive home the message that deviating from your idealistic picture of your future can still have some pleasant surprises hiding where you least expect them.

While critics at the time had mixed feelings about the film, audiences continue to revisit "13 Going On 30" years later because of its nostalgia, whimsy, and charm.

After finding success in sitcoms early in his career, Ryan Reynolds took plenty of roles that showed off his silliness, snarkiness, and charisma. And though many remember 2009's maligned "X-Men Origins: Wolverine" (which would eventually lead to bigger and better superhero things), the Vancouver native also showed that he was tailor-made to lead rom-coms like "The Proposal," "Just Friends," and "Van Wilder." But out of his many offerings in the genre from this time period, "Definitely, Maybe" might stand out as one of the best.

The 2008 film follows Reynolds as Will Hayes as he tells his 10-year-old daughter Maya (played by Abigail Breslin) how he met and married her mother. However, ahead of her parents' upcoming divorce, Maya wants Will to recount his romantic journey through New York City in the early 1990s to solve the mystery of how they ended up where they are in the present and where they're going next.

Taking a page out of the "How I Met Your Mother" playbook, "Definitely, Maybe" is an underrated millennial rom-com with an incredible cast that freshens up old tropes while still delivering the warm and cozy feeling that comes with the genre.

"Pride and Prejudice," Hugh Grant, and Richard Curtis have already been mentioned on this list, but we've come back around to all of them thanks to "Bridget Jones's Diary." Based on the 1996 novel by Helen Fielding that was loosely inspired by Jane Austen's classic tale, the 2001 rom-com chronicles the life of Renée Zellweger's titular thirty-something heroine as she finds herself intertwined in a love triangle with two very different yet appealing suitors played by Grant and Colin Firth.

Much like The Doctor, the Spice Girls, or Paddington Bear, Zellweger's Academy Award-nominated portrayal of Bridget Jones has become a British cultural icon. But moreover, due to her awkwardness, aspirations of self-improvement, and occasionally negative self-talk, she has become a quintessential rom-com icon as well. Incredibly relatable and insanely quotable, generations of fans have connected with this story in a way that has kept the franchise alive for three more sequels, the latest of which debuted on Peacock in 2025.

Throughout the history of entertainment, there has been an overwhelming bias towards New York City. Many other US cities probably challenge the notion that it's more enchanting than they are. However, sometimes a movie comes along that makes even the harshest critic of the East Coast metropolis believe in its magic. In terms of 2000s rom-coms, "Serendipity" certainly falls into that category.

Taking its title from the word meaning an unexpected yet fortuitous occurrence, the film stars John Cusack and Kate Beckinsale as two people who were searching for a pair of gloves in a department store. Instead, they essentially find their soulmate. But even after Jonathan Trager and Sara Thomas try to move on after that magical evening together in the Big Apple, the universe finds a way to bring them back together down the line as they are each on the verge of life-changing developments.

On one hand, "Serendipity" is fluffy and charming. But it's also hopeless romantic fuel that burns with the message that everyone is destined to find their person. The idea may be a little corny or old-fashioned, but that can be gold to fans of this genre.

For the films that he wrote and directed in the early 2000s, Judd Apatow took romantic comedies and disguised them as gross-out sex comedies that men gravitated towards. In reality, the filmmaker was adding a more realistic nuance while blending different sub-genres in the broad comedy category. Because of this, "Knocked Up" really holds up as a cultural snapshot of this time period, an expansion of what can be considered a rom-com, and the tolls various stages of dating can take on a modern couple.

In the film, Katherine Heigl and Seth Rogen's Alison Scott and Ben Stone meet at a bar during a night on the town and go home together for a one-night stand. However, due to some miscommunication, the pair have unprotected sex, which results in Allison getting pregnant. The relatively grounded plot and likable ensemble of "Knocked Up" greatly endears the film to its audience. It also helps that there are so many hysterical and very quotable moments, but it should receive some credit for contributing to a larger conversation about the anxieties surrounding adulthood and commitment.

When you look at the structure of a romantic comedy, the two parts that audiences constantly revisit are the meet-cute (the adorable moment when our romantic leads meet for the first time) and the happily ever after. So what happens when a movie adopts a gimmick where the meet-cutes are non-stop? In theory, that's what you get in "50 First Dates," starring Adam Sandler and Drew Barrymore. However, in execution, the 2004 rom-com from filmmaker Peter Segal shows a much softer side of the leading man that is enhanced by his "Wedding Singer" co-star.

"50 First Dates" follows womanizing veterinarian Henry Roth as he sets his sights on art teacher Lucy Whitmore. But even after he finds out about her amnesia that causes short-term memory loss, Henry becomes determined to win over Lucy as many times as it takes so they can be together. The film is memorable thanks in large part to the leads' excellent chemistry, plenty of adorable moments between the couple that extend past the meet-cutes, and a solid supporting cast that includes Sean Astin, Blake Clark, and Amy Hill. And with the story taking place in front of the romantic backdrop of Hawaii, this one pulls on all the right heartstrings.

Audiences have seen plenty of movies where the leads are brought together by some kind of wager that one or sometimes both parties are unaware of initially. When it comes to 2000s rom-coms, one film that comes to mind is "How to Lose A Guy in 10 Days." However, while that would certainly earn a top 20 spot on a list like this, Will Smith and Eva Mendes' "Hitch" ranks a little bit higher because its characters are a little more well-intentioned.

The 2005 movie casts the "Fresh Prince of Bel-Air" star as professional date doctor Alex Hitchens, who tries to help awkward but genuine clients like Kevin James' Albert Brennaman connect with the partner of their dreams. But when he applies his tried-and-true methods to gossip columnist Sara, Hitch proves that the dating game still has its fair share of curveballs for even the most veteran players. Of course, things become more complicated as Sara begins investigating Hitch and his professional motives for a story based on a bad source.

Predictable? Sure, but "Hitch" is so charming that the fans have no problem going along for the ride. Plus, it says to hell with conventional beauty or class standards, which was a refreshing take for a rom-com back then.

Before the world became obsessed with "K-Pop Demon Hunters," BTS, or the work of filmmaker Park Chan-wook, "My Sassy Girl" played a key role in starting the Korean new wave of entertainment that is still going strong today. The 2001 South Korean romantic comedy is based on the real-life relationship between blogger Ho-sik Kim and his ex-girlfriend. After turning his blog posts into a novel, he collaborated with filmmaker Kwak Jae-yong to create the movie that would go on to become both the highest-grossing comedy of all time and one of the top five highest-grossing films ever in South Korea at the time.

In the film, engineering student Gyeon-woo is unlucky in the romance department. Though his aunt wants to set him up, his life is thrown for a loop when he saves a drunk girl from falling off a subway platform and getting hit by a train. From there, Gyeon-woo endures being maced by police, being held hostage by an AWOL soldier, and reading The Girl's amateur screenplays before uncovering his true feelings for her. But after her parents reject their relationship, the couple goes through a rollercoaster of emotions over the next few years filled with laughs, heartbreak, and surprises.

Due to its many accolades and cult following, "My Sassy Girl" drew comparisons to James Cameron's "Titanic" when it was released, and many remakes were made around the world in Japan, China, India, America, and beyond in an effort to recreate its success. But as is usually the case, nothing compares to the original.

As the old children's rhyme goes, "First comes love, then comes marriage." For 30-year-old Fotoula "Toula" Portokalos, it felt like she would never get to that second part because of her overbearing, old fashioned, and sometimes embarrassing Greek family. But after meeting high school teacher Ian Miller, she tries to keep their relationship a secret since her relatives would disapprove of her dating a non-Greek man. Of course, this all goes out the window when Ian and Toula decide to get married, causing hilarity to ensue in "My Big Fat Greek Wedding."

The 2002 rom-com directed by Joel Zwick and written by (and starring) Nia Vardalos showcases how cultural identity and heritage can play a large part in romance. It also serves as a great example that the themes and feelings conveyed here are universal in their specificity, a tradition carried on in the genre by later films featuring weddings like "Crazy Rich Asians," the 2022 remake of "Father of the Bride," and "Monsoon Wedding."

After playing a supporting role in "How I Met Your Mother" and various Judd Apatow projects, Jason Segel broke out as a leading man in his own right in "Forgetting Sarah Marshall." The 2008 rom-com follows composer Peter Bretter as he goes on a Hawaiian vacation after his five-year relationship with a prominent TV star comes to an end. However, when his ex shows up with her new rockstar boyfriend, Peter gets closer to hotel concierge Rachel (played by Mila Kunis), who encourages him to try new things.

Like "Knocked Up" before it, "Forgetting Sarah Marshall" has plenty of raunchy humor. As if bearing himself emotionally wasn't enough, Peter is seen completely naked at various points in the film. But because the movie has so much heart and knows its characters well, moments like that fit seamlessly with the sincerity, hilarity, and masterful vampire puppetry.

Many consider Marc Webb's "(500) Days of Summer" to be an unconventional rom-com because of the non-linear storytelling, the changes in style throughout the movie, and the honesty with which it portrays being in the trenches of love. But the thing that makes the film, starring Joseph Gordon-Levitt and Zooey Deschanel, so outstanding is the self-absorbed, unreliable narrator telling the story of his 500-day-long relationship with a woman he dated.

Some may perceive JGL's aspiring architect to be an innocent victim of heartbreak at the hands of a manic pixie dream girl. But Tom Hansen is actually projecting his image of Summer Finn onto her throughout their relationship and only hears what he wants to hear. The script uses rom-com tropes to paint a certain picture of this couple, only to unveil the reality of the situation by slightly shifting the POV. And at the end, Tom basically learns nothing as he gets ready to do it all again.

The 2009 film has so much to say about modern dating culture. After putting a mirror up to the audience who finds Tom relatable, it's just endlessly fascinating to see who's ready to hear it when the credits roll.

The words "warm" and "cozy" have been used often in this list to describe the feelings that rom-coms give to their audience. But for Kate Winslet and Cameron Diaz as Iris Simpkins and Amanda Woods in "The Holiday," these words describe how they want to feel after they escape their deteriorating realities and switch houses to experience how the other lives across the pond.

Also featuring Jack Black and Jude Law as their love interests, this charming cast delivers a textbook Nancy Meyers romantic comedy. Parts of the story even outline the best way to describe the rom-com structure as Iris learns the ins and outs of screenwriting from Amanda's neighbor, Arthur Abbott. And with a delightful score orchestrated by Hans Zimmer as the bow to tie it all together, "The Holiday" is exactly what you want when seeking out a light, endearing love story, especially around the holidays.