25 2000s Rom-Coms That’ll Make You Believe Love Still Exists
I’m just going to say it: the 2000s (and ‘90s) were the golden age of romantic comedies. Were they cringey? Sure. You wouldn’t catch me dead in a karaoke face-off belting out You’re So Vain with increasing aggression. But were they wholesome? Oh, yes. It’s Henry’s persistence in 50 First Dates despite a girl who forgets him every day. It’s Jenna and Matty reconciling with a real-life version of her pink dream house in 13 Going on 30. The way Jake Perry refuses to sign the divorce papers because he’s still in love with Melanie after all these years in Sweet Home Alabama. In today’s day and age, dating is exhausting. Whether you’re on Raya or Hinge, everyone is feeling the slog of the apps. We’ve turned to blind dates, speed dating and even contra-dating—with middling results. What better consolation, then, to crawl home after a terrible date and watch Viola slowly fall for Duke (She’s the Man) or Bridget Jones bumble between her love triangle starring Colin Firth and Hugh Grant? Below, I’ve rounded up 25 of the best 2000s rom-coms (spanning from 2000 to 2010) that make me believe that love still exists. Hopefully, they do the same for you.
Are You Dating a Soonicorn? And If So, Should You Dump Them?
1. How to Lose a Guy in 10 Days
Year: 2003
Who’s in It: Kate Hudson, Matthew McConaughey
Run Time: 1 hour 53 minutes
How to Lose a Guy in 10 Days is one of my favorite 2000s rom coms of all time—if not my ultimate pick. Andie Anderson is an advice columnist at a glossy women’s fashion magazine, longing to tackle more pressing, serious subjects in her writing. She strikes a deal with the editor-in-chief: Write a column about how to get a guy out of your life in ten days, and she has free reign for her next assignment. Andie’s just not expecting that the dashing Benjamin Barry has machinations of his own. It grossed $177.5 million, far exceeding its $50 million budget. And thus, Carly Simon’s You’re So Vain lives in infamy with a yellow Carolina Herrera gown and matching Harry Winston necklace valued at $6 million.
2. 13 Going on 30
Year: 2004
Who’s in It: Jennifer Garner, Mark Ruffalo
Run Time: 1 hour 38 minutes
Say it with me: 30, flirty and thriving. Jenna Rink, played by the effervescent Jennifer Garner, has just one wish—to be 30 and cool. With the help of some magical wish dust, she gets exactly what she wants, only to discover that maybe what she wanted was right there all along. As an adult, Jenna is the executive editor of a floundering fashion magazine. She calls on the help of old friend Matty Flamhaff as she adjusts to grown-up life with a teenager’s mindset. From an exuberant and iconic rendition of Michael Jackson’s Thriller to a happily-ever-after complete with a pink house, 13 Going on 30 is my number two pick for best 2000s rom coms of all time. After all, there’s no better realization than understanding that the best person to be is yourself.
3.The Proposal
Year: 2009
Who’s in It: Sandra Bullock, Ryan Reynolds, Betty White
Run Time: 1 hour 48 minutes
What would you do for the career of your dreams? In 2009’s The Proposal starring Sandra Bullock and Ryan Reynolds, for Andrew (Reynolds), that means marrying his domineering boss, Margaret (Bullock). If he doesn’t, she’ll be deported to her native Canada and Andrew will be fired by Margaret’s successor, dashing his hopes of becoming a book editor. The film netted $317 million at the box office, and has plenty of memorable scenes when the couple travels to Andrew’s hometown of Sitka, Alaska. Among them are Margaret’s pow-wow with Andrew’s grandma, Annie (Betty White), repeated run-ins with a local exotic dancer and a treacherous climb down a ladder with a Birkin bag in tow. While it received mixed reviews from critics, the Los Angeles Times called it a “cheeky update of The Taming of the Shrew.”
4. 50 First Dates
Year: 2004
Who’s in It: Adam Sandler, Drew Barrymore
Run Time: 1 hour 46 minutes
The iconic duo Drew Barrymore and Adam Sandler reunited after The Wedding Singer for 50 First Dates. Though Rotten Tomatoes criticizes the fact that “gross out humor” monopolizes the story line, I must make the case for it. What’s more romantic than knowing you’ll need to make someone fall in love with you every day for the rest of your life, and pursuing them anyway? That’s exactly what marine veterinarian Henry Roth (Sandler) does when Lucy Whitmore (Barrymore), a woman who suffers from short-term memory loss, walks into his life. Sweeter still: After Barrymore read the script, she wrote Sandler a letter suggesting they reunite following The Wedding Singer. For their roles, the pair won the Best On-Screen Team award at the 2004 MTV Movie Awards.
5. The Wedding Planner
Year: 2001
Who’s in It: Jennifer Lopez, Matthew McConaughey
Run Time: 1 hour 44 minutes
J.Lo has worn her fair share of wedding dresses over the span of her career, and the one she dons in The Wedding Planner was ranked nine out of ten by PureWow senior editor Dana Dickey. But though the dress may be charmingly simple, the plot is not. Mary Fiore (Lopez) finds herself planning the wedding of heiress Fran Donolly to the latter’s long-term boyfriend, Eddie (McConaughey). When Mary discovers that it was Eddie who saved her from a careening dumpster just days earlier, chaos ensues as she realizes that she’s falling in love with him—all while Mary’s own father is trying to set her up with someone else. At the time of release, the film wasn’t well received, with Lopez earning a nomination for Worst Actress at the 22nd Golden Raspberry Awards. Today, though? Classic.
6. She’s the Man
Year: 2006
Who’s in It: Amanda Bynes, Channing Tatum
Run Time: 1 hour 45 minutes
If there’s one type of movie I love more than a Jane Austen adaptation or Wes Anderson film, it’s a riff on the bard. Inspired by Shakespeare’s Twelfth Night, the plot of She’s the Man takes off when Viola Hastings’s (Bynes) twin brother, Sebastian, ditches school to go to London with his band. Meanwhile, Viola dreams of playing soccer for the North Carolina Tar Heels, but her high school has disbanded the girls’ soccer team. Taking Sebastian’s place will give her the change to play. Once transformed into her brother, Viola meets the dashing team captain, Duke, who reveals he’s afraid of talking to girls. As the pair bond over soccer, Viola finds herself falling in love…and caught in a sticky love triangle. Armed with a box of tampons (they’re great for nosebleeds), her sports gear and relentless determination to play, Viola will need to figure out how—and when—to reveal the truth. When the film was cast, Bynes pushed for Tatum to play Duke, despite the fact that he was much older than the others at the time. She claims, according to CinemaBlend, that she knew he was the one after seeing Tatum in a Mountain Dew commercial.
7. 500 Days of Summer
Year: 2009
Who’s in It: Joseph Gordon-Levitt, Zooey Deschanel
Run Time: 1 hour 35 minutes
“For better or worse, 500 Days of Summer is SO 2009 it hurts,” says PureWow senior food editor Katherine Gillen. “It’s peak millennial hipster culture, from the manic pixie dream girl to the imagined Hall and Oates flash mob and the indie soundtrack (which is good, save for The Smiths).” The movie stars Joseph Gordon-Levitt and Zooey Deschanel as Tom Hansen and Summer Finn, who are both employees at a greeting card company. Moving through dual timelines, Tom reflects on the 500 days of his relationship with Summer while trying to figure out how to win her back. The movie was a sleeper hit, earning $60 million on a $7.5 million budget. It was an indie flick that premiered at Sundance and was later distributed by Fox Searchlight Pictures. Earning favorable comparisons to Annie Hall and High Fidelity, 500 Days of Summer is now considered a cult classic. Gordon-Levitt also earned a Best Actor Golden Globes nod for his performance.
8. Love Actually
Year: 2003
Who’s in It: Hugh Grant, Emma Thompson, Colin Firth, Liam Neeson, Keira Knightly
Run Time: 2 hours 9 minutes
“Love Actually is one of my favorite movies,” says PureWow assistant editor Delia Curtis. “It’s definitely got its major flaws (i.e. trying to steal your best friend’s wife, cheating on your spouse). But there’s just something about a star-studded film with intertwined storylines centered around the same theme that has my heart. I will also never get over the scene of young Thomas Sangster running through the airport with his stepdad so that he can tell the girl he likes that he has a crush on her. Plus, the All I Want For Christmas Is You musical moment during the school nativity play is iconic with Emma Thompson’s on-screen child playing the first lobster.”
9. The Holiday
Year: 2006
Who’s in It: Cameron Diaz, Jude Law, Kate Winslet, Jack Black
Run Time: 2 hours 18 minutes
Iris Simpkins (Kate Winslet) and Amanda Woods (Cameron Diaz) are two women on opposite sides of the world who are crossed in love—the former’s ex-boyfriend is marrying someone else, the latter’s has just cheated on her. The women agree to a house swap, so Iris heads to LA and Amanda to the English countryside. With the holidays approaching, the women fall in love with their new neighbors, Graham (Law)—who happens to be Iris’s brother—and Miles (Black), Amanda’s colleague and a film composer. This is one of my top 2000s rom coms to play during the holiday season, if for the Christmas vibes alone. The Holiday was one of Winslet’s early forays into films that weren’t period dramas, and she prepped for the role by watching 1940s screwball comedies like His Girl Friday and The Philadelphia Story.
10. Bride Wars
Year: 2009
Who’s in It: Kate Hudson, Anne Hathaway, Chris Pratt
Run Time: 2009
When a clerical error has best friends Liv and Emma gunning for the same wedding date, they find their friendship at stake as the bridezilla in each of them comes out full force. “Bride Wars is so cheesy it’s borderline cringey, but Anne Hathaway and Kate Hudson have such great comedic timing and charm that it makes for a fun watch,” says PureWow vice president of editorial Candace Davison. “It’s a good movie to have going on in the background after a long day, when your brain is fried and you just need something silly and lighthearted as you mentally recoup.” While the movie was derided by critics (indeed, even Davison, who watched it in 2009, isn’t sure it holds up now), it was a box office success, raking in over $115 million.
11. My Big Fat Greek Wedding
Year: 2002
Who’s in It: Nia Vardalos, John Corbett
Run Time: 1 hour 35 minutes
Starring Nia Vardalos and John Corbett (of Sex and the City fame), My Big Fat Greek Wedding is a slapstick story with the ugly duckling transformation trope. Shy, unmarried Toula’s (Vardalos) life is turned upside down when she starts dating Ian (Corbett). To her family’s chagrin, he’s not Greek. In the courtship that follows, Ian must hilariously prove his worth to Toula’s overbearing father. I find it a heartwarming film about staying true to your roots and to who you are without compromising either. The movie was produced by Tom Hanks on a $5 million budget and became a sleeper hit, ultimately grossing over $368 million, making it one of the 21st-century’s top-earning romantic films.
12. Sweet Home Alabama
Year: 2002
Who’s in It: Reese Witherspoon, Josh Lucas, Patrick Dempsey
Run Time: 1 hour 49 minutes
Fresh off the successful release of Legally Blonde, Reese Witherspoon took the lead in Sweet Home Alabama as fashion designer Melanie Carmichael. When Carmichael’s boyfriend, the wealthy Andrew Hennings (Dempsey) proposes, her answer is a resounding yes. But first, she’ll need to go back to Alabama to get her husband, Jake Perry, to finally sign the divorce papers she’d served him years ago. This movie had me in a total puddle as the characters worked to figure out what it means to be in love—and the price you’ll pay so you don’t have to let it go. Sweet Home Alabama made $180 million on a $30 million budget and—for all you Audrey Hepburn fans—was the first movie to film in Tiffany & Co. since Breakfast at Tiffany’s in 1961.
13. Bridget Jones’ Diary
Year: 2001
Who’s in It: Renée Zellweger, Colin Firth, Hugh Grant
Run Time: 1 hour 37 minutes
“I just rewatched Bridget Jones’s Diary on a plane and while yes, it’s flawed in many ways (the emphasis on Bridget’s weight, OMG), I do adore so many elements about it,” gushes PureWow’s senior director of special projects and royals, Rachel Bowie. “Bridget’s narration, her emergency friendship committee, heck, the sexiness that is Colin Firth. It’s silly and fun and I absolutely love Renée Zellweger as someone so charming and unselfconscious. You can’t help but cheer her on!” Loosely based on Jane Austen’s Pride & Prejudice, the film follows 32-year-old Bridget Jones as she bumbles her way through life and love. For her performance, Zellweger earned an Academy Award nomination for Best Actress. Since her debut, Bridget herself has been declared a British pop culture icon.
14. Wedding Crashers
Year: 2005
Who’s in It: Owen Wilson, Vince Vaughn, Isla Fisher, Rachel McAdams, Christopher Walken, Will Ferrell
Run Time: 1 hour 59 minutes
With funnyman Will Ferrell in the mix, you know the movie will have you in stitches. Bad boys and divorce mediators John Beckwith (Owen Wilson) and Jeremy Grey (Vince Vaughn) hatch a plan to crash the wedding of the daughter of the U.S. Secretary of the Treasury. Their MO with every wedding they crash is to sleep around, so trouble arises when both find themselves romantically entangled with the bride’s sisters. “Wedding Crashers cracked me up, but years later, the scenes that resonate are...every one with Will Ferrell,” Davison says. “To this day, I imagine him yelling ‘Mom, MEATLOAF!’ any time my kid urgently shouts for me in the middle of the night, just to tell me she’s out of water. It’s light on the rom, heavy on the com, and I’m OK with that.” Wedding Crashers was 2005’s sixth highest-grossing film at $288 million, and was also a critical success, with Stephen Farber writing in The New York Times that the movie heralded the return of R-rated comedies.
15. Maid in Manhattan
Year: 2002
Who’s in It: Jennifer Lopez, Ralph Fiennes, Tyler Posey, Natasha Richardson
Run Time: 1 hour 45 minutes
“I LOVE Maid in Manhattan,” says PureWow associate commerce strategist Jael Rucker. “It has all the classic elements of being a 2000’s rom-com and is undoubtedly one of Jennifer Lopez’s most memorable films.” The plot is a contemporary Cinderella story, with maid Marisa Ventura (Lopez) falling in love with senate candidate Christopher Marshall (Fiennes). Though it received mixed reviews, Maid in Manhattan ultimately earned $154 million at the box office.
16. Pride & Prejudice
Year: 2005
Who’s in It: Keira Knightly, Matthew Macfadyen, Carey Mulligan, Rosamund Pike
Run Time: 2 hours 7 minutes
OK, yes, Pride & Prejudice isn’t top of mind when you think of 2000s rom coms, but I will make the case for my favorite book of all time. (I’ve read it 20 times.) This adaptation was released in the mid-2000s and was directed by the cinematic genius that is Joe Wright, led by the stunning Kiera Knightly as our heroine. And, it’s funny, people! Try watching Mrs. Bennett fling pudding onto a dashing party guest, listen to Mr. Collins compliment the excellence of the boiled potatoes and witness Mr. Darcy’s fist-clenching moment that could give Arthur a run for his money and try not to laugh, I dare you. Pride and Prejudice was a smashing success, earning four Academy Award nominations (including Best Actress for Knightley), plus a BAFTA Award for Outstanding Debut by a British Writer, Director or Producer for Wright. But here’s the real tea: On-screen love interests Jane Bennett (Pike) and Charles Bingley (Simon Woods) were exes in real life.
17. Juno
Year: 2007
Who’s in It: Elliot Page, Michael Cera, Jennifer Garner
Run Time: 1 hour 31 minutes
Upon its release in 2007, Juno garnered critical acclaim and box office success, raking in over $232 million and winning the Academy Award for Best Original Screenplay. It also scored nominations for Best Picture, Best Director and Best Actress. I watched it ages ago, but still recall the heartwarmingly chaotic coming-of-age story of Juno MacGuff (Page), a teenager who finds her life on a detour when she discovers she’s pregnant by her friend, Paulie Bleeker (Cera). Though she finds a couple to adopt the baby, problems soon arise as tensions flare between Juno and Paulie and Vanessa (Garner) and Mark (Jason Bateman). Ultimately, it’s a story about two women choosing their own paths—whether that be falling in love or flying solo.
18. The 40 Year-Old Virgin
Year: 2005
Who’s in It: Steve Carell, Paul Rudd, Seth Rogen
Run Time: 1 hour 56 minutes
In one of Steve Carell’s most iconic performances, he plays 40-year-old Andy Stitzer, a shy electronics store employee who can’t talk to women. After his coworkers Jay, David and Cal discover his secret, he is beset with advice, including the now infamous chest wax and a date with a prostitute. Eventually, he meets single mother Trish Piedmont, and romance blooms. The 40 Year-Old-Virgin was named one of the American Film Institute’s top ten films of 2005, earning over $177 million.
19. The Notebook
Year: 2004
Who’s in It: Ryan Gosling, Rachel McAdams
Run Time: 2 hours 1 minute
Based on Nicholas Sparks’s novel of the same name (it’s now on Broadway, too), The Notebook stars Ryan Gosling and Rachel McAdams as lumber mill worker Noah Calhoun and heiress Allison Hamilton. In a Romeo and Juliet-like twist, the two star-crossed lovers are kept apart, divided by class. Years later, Allie sees Noah in the local paper, as the former has fulfilled his dream of restoring the old Windsor Plantation. Though engaged, she travels back to the town where they met, and they rekindle their romance. The film was a success, winning the MTV Movie Award for Best Kiss. It is also one of the highest-grossing romantic films of all time.
20. 27 Dresses
Year: 2008
Who’s in It: Katherine Heigl, Malin ?kerman, James Marsden
Run Time: 1 hour 51 minutes
You know the saying, “always a bridesmaid, never the bride”? Well, Jane Nichols (Katherin Heigl) knows that refrain well, having been a bridesmaid 27 times. When her sister, Tess (Malin ?kerman), becomes engaged to the former’s boss—whom she secretly loves—Jane finds herself being interviewed by wedding reporter Kevin Doyle (James Marsden). His story in the local paper about bridezilla Tess and Jane as the perennial bridesmaid causes tensions to boil over, leading to the question—will Jane get her happily ever after? Though it received mixed reviews, 27 Dresses ultimately earned $162 million on its $30 million budget.
21. A Cinderella Story
Year: 2004
Who’s in It: Hilary Duff, Chad Michael Murray, Jennifer Coolidge
Run Time: 1 hour 35 minutes
A retelling of a classic fairytale, this movie is set in the San Fernando Valley with plenty of high school drama to go around. Sam Montgomery (Hilary Duff) suffers under the tyrannical rule of her stepmother after her father dies. Her only solace is her dream to attend Princeton and become a writer, and an online friendship with “Nomad.” As it turns out, her mysterious friend is actually her school’s secretly unhappy quarterback who wants to attend Princeton, too. They meet at the school dance, though in typical Cinderella fashion, Sam is in disguise and cannot reveal herself before she must rush home. Like all good fairytales, there’s a good ending. Though widely panned at release, A Cinderella Story now stands as a cult classic.
22. Love Don’t Cost a Thing
Year: 2003
Who’s in It: Nick Cannon, Christina Milian, Kenan Thompson, Steve Harvey
Run Time: 1 hour 41 minutes
Nick Cannon plays decidedly uncool but highly intelligent high schooler Alvin Johnson who’s scheming to buy himself some points with the in crowd. The pretty and popular Paris Morgan (Christina Milian) agrees to be his fake girlfriend for two weeks in exchange for Alvin repairing her mother’s car, which she and her boyfriend have wrecked. With Paris’s stamp of approval, Alvin rapidly climbs the social ladder, but at the price of his friendships. And, of course, somewhere along the way of playing pretend, the pair find out they’re actually in love.
23. Punch Drunk Love
Year: 2002
Who’s in It: Adam Sandler, Philip Seymour, Emily Watson
Run Time: 1 hour 35 minutes
If Adam Sandler is involved, you know it’s going to be raunchy and romantic. In Punch Drunk Love, he stars as Barry Egan, an entrepreneur who sells themed toilet plungers and is bullied by his seven sisters. After a phone sex escapade goes awry, he finds his budding relationship with Lena (Emily Watson) at stake. Of course, there are other absurdities, including a frequent-flyer miles scam involving pudding and a mattress store owner who’s actually an extortionist. Though it bombed at the box office, the movie has been cited by many a director and actor as their favorite, and it’s considered the film that catapulted Sandler to star in more unconventional roles.
24. Under the Tuscan Sun
Year: 2003
Who’s in It: Diane Lane, Sandra Oh, Raoul Bova
Run Time: 1 hour 53 minutes
Freshly divorced and without a home, writer Frances Mayes (Diane Lane) is urged by her friends to take an Italian vacation to forget her troubles. Serendipitously, she becomes the owner of a crumbling villa, and of course, she finds herself with handsome neighbor, Marcello (Raoul). As she builds a new life for herself in the Italian countryside, Frances feels that love couldn’t be further away—but she soon finds that it’s not as elusive as she thinks. For her role as Frances, Lane earned a Golden Globes nomination for Best Actress-Motion Picture Comedy or Musical, which was also highly lauded by critics.
25. Last Holiday
Year: 2006
Who’s in It: Queen Latifah, Halle Bailey, LL Cool J
Run Time: 1 hour 52 minutes
Last Holiday is loosely based on a 1950s British film with the same title and finds Queen Latifah as Georgia Byrd, a shy department store employee secretly pining after her co-worker, Sean (LL Cool J). After Georgia receives a devastating (though mistaken) medical diagnosis, she liquidates her assets, determined to spend her “final weeks” in adventure and luxury at an upscale spa resort in Europe. While there, she wins over the hearts of staff and guests alike—except for the owner of the department store where she works. Learning of her diagnosis, Sean, who has also been pining for Georgia, flies over to confess his love. Of course, obstacles spring up as soon as he lands—but isn’t that what makes love worth fighting for?
