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Love was in the air in the 2000s — and so were memorable meet-cutes, slightly contrived conflicts, and satisfying happy endings. That decade produced rom-coms that taught a whole generation a thing or two about love, and have, for the most part, aged like fine wine.
The movies below are the best of this era, and by “the best,” we don’t mean the most critically acclaimed (though some of them do hold their own among cinema’s greatest). Instead, we mean stories that sweep you away and restore your faith in love — all while making you laugh along the way.
Get the popcorn ready. Here are 15 of the best rom-coms of the 2000s.
1. 13 Going On 30 (2004)
Jennifer Garner shines in this 2004 classic, in which a 13-year-old Jenna Rink’s wish to wake up thirty, flirty, and thriving suddenly comes true, and all hell breaks loose.
For those of us who first saw this film as teens, watching it again when we’re closer to thirty (and, hopefully, also flirty and thriving) is an unmatched experience.
2. Mamma Mia! (2008)
This movie has everything: Meryl Streep as Donna and Amanda Seyfried as her daughter Sophie; Pierce Brosnan, Colin Firth, and Stellan Skarsgård as Sophie’s three possible fathers; a gorgeous Greek location; and a perfect soundtrack based on ABBA songs, with additional music from ABBA member Benny Andersson. My, my, how can I resist you?
The film follows Sophie and Donna as they try to figure out who Sophie’s real father is in time for her upcoming wedding — and chaos ensues. Its sequel, Mamma Mia! Here We Go Again, was released in 2018.
3. Bridget Jones’s Diary (2001)
Bridget Jones’s Diary was based on a 1996 novel of the same name, which was, in turn, inspired by Jane Austen’s Pride and Prejudice. Renée Zellweger’s Bridget is charming and relatable as she finds herself in the middle of a love triangle between her boss Daniel (Hugh Grant) and the snobbish Mark (Colin Firth).
The film, which went on to start a successful trilogy, is a celebration of being just as you are.
4. Ella Enchanted (2004)
The eponymous Ella’s romance with Prince Char features heavily in the trailer, and is certainly one of the most entertaining parts of this 2004 classic.
But in telling the story of a girl cursed to obey every command given to her, the film also says a lot about consent, autonomy, and gender. It also comments on racism, classism, and slavery — while pulling off a couple of memorable song numbers.
5. Imagine Me and You (2005)
You know what they say: Never let your husband stop you from finding your wife.
In this queer rom-com about love at first sight, Luce and Rachel first meet on Rachel’s wedding day to Heck, for which Luce is a florist. Lena Headey and Piper Perabo’s performances are top-notch, and the film takes all the familiar rom-com tropes and queers them to perfection.
The best part is that everybody walks away from the mess with a happy ending.
6. Brown Sugar (2002)
Brown Sugar, which stars Taye Diggs and Sanaa Lathan, is a criminally underrated rom-com, and is as much an update to the beloved friends-to-lovers trope as it is a love letter to rap and hip-hop.
In this film, lifelong friends Sidney and Andre share a love for New York’s hip-hop scene, with Sidney appointed as editor-in-chief of hip-hop magazine XXL, and Dre working as an A&R for Millennium Records. Things change as they realize that hip-hop isn’t the only thing that binds them together.
7. Legally Blonde (2001)
Featuring Reese Witherspoon at her best, this movie spawned a thousand GIFs, inspired a generation of lawyers, and changed the way many thought about the color pink.
Legally Blonde’s unabashedly feminine protagonist is Elle Woods, who enters law school to win back an ex-boyfriend, but soon realizes that he is not worthy of her love and decides to succeed for herself. The film neither disses nor praises hyperfemininity — it simply never treats a love for pink and success in legal practice as mutually exclusive, almost turning to the audience and daring them to say different.
It’s a film that tackles female friendship, gender stereotypes, and even workplace harassment, and afterward, says, “What, like it’s hard?”
8. A Cinderella Story (2004)
Cinderella remakes are left and right (including Ella Enchanted above), but there’s something about this one, starring Hilary Duff, Chad Michael Murray, the Jennifer Coolidge, and Regina King, that makes for a fantastic rewatch as an adult.
In it, Sam finds comfort from the torment of her mother and step-sisters by connecting with an anonymous pen pal online. She doesn’t know that he’s actually the popular, but secretly just as miserable, jock Austin Ames, and the world turns upside down as they grow closer together.
Plus, watching Hilary type L-O-L on an old cellphone is peak nostalgia.
9. Maid in Manhattan (2002)
Maid in Manhattan centers Marisa Ventura, a struggling single mom who falls for rising politician Chris Marshall after he stays in the hotel she cleans. The problem is, he thinks she’s also a hotel guest.
Jennifer Lopez’s rom-com debut is opposite Ralph Fiennes (who went on to play, of all characters, Lord Voldemort, which is hard to unsee).
The film has its flaws, but the opening sequence — which moves from shots of the iconic New York City skyline and zooms further into the city’s less than glamorous neighborhoods — is pretty cool, and JLo shines with every line and meaningful look.
10. How to Lose a Guy in 10 Days (2003)
Rom-coms get a lot of flak for their contrived plots, but that’s where the fun is — and How to Lose a Guy in 10 Days is a testament to that.
In it, you have a woman on a mission to prove she can get a guy to break up with her in 10 days, and a man convinced that he could get any woman to fall in love with him in 10 days. Of course, they meet and date each other. Add Matthew McConaughey and Kate Hudson’s charm, and you’ve got a rom-com classic.
11. Music and Lyrics (2007)
After Bridget Jones’s Diary, Hugh Grant came back opposite Drew Barrymore in this charming rom-com about a washed-up ‘80s pop star and the surprisingly creative lady who waters his plants. The two work together to craft his comeback song — giving us not just a banger, but a cute love story to boot.
“It’s impossible to hate,” Grant said, in a 2021 interview on The Drew Barrymore Show. “We’re so good in it, and so charming.”
12. Juno (2007)
Juno is Elliot Page’s breakout film in a career full of highlights. The film follows the eponymous teenager as she gets pregnant by her bestfriend Paulie and finds a couple who would adopt her baby.
With a solid script, fantastic performances, and a great soundtrack, the film is a critical and commercial success that continues to be a great rewatch for a lazy afternoon.
13. Enchanted (2007)
Enchanted, starring Amy Adams, Patrick Dempsey, and James Marsden, is both an homage to and a parody of the classic Disney animated movie. In it, we follow Giselle as she is pushed out of the animated kingdom of Andalasia and transformed into a live-action version of herself in real-life New York City.
The film combines traditional animation, CGI, live-action filmmaking, fantastic performances, and great music to give us a heart-warming rom-com to watch again and again.
14. 500 Days of Summer (2009)
500 Days of Summer opens by telling you exactly what’s going to happen, and is clear about what the film isn’t: A love story.
In this refreshing rom-com, Tom is a hopeless romantic who is caught completely off-guard when his girlfriend, Summer, dumps him. Everything is not what it seems, especially from behind Tom’s rose-colored glasses, and the resulting film is one that stays with you long after the credits roll.
15. The Proposal (2009)
Silly and formulaic in all the best ways, The Proposal follows Margaret and her long-suffering assistant Andrew as they become fake engaged lovers in an effort to secure Margaret a US visa. They just have to trick his family and the government, which leads to plenty of laugh-out-loud moments.
Sandra Bullock and Ryan Reynolds shine individually and as a team, and it’s hard to resist their chemistry all these years later.
