There’s something comforting about rewatching your favorite movies. That wrings especially true for romantic comedy movies from any era, but there’s just something about 2000s rom coms that make us want to return back time and time again. Whether you’re looking for a Valentine’s Day movie idea or are just in the mood for some love and laughs, this list of the best rom coms from the 2000s to watch (or rewatch) won’t disappoint.
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On this list you’ll find a variety of rom coms to choose from the early 2000s up until the end of the aughts. And while some of these you’ve almost certainly watched before, hopefully you’ll also find a few new flicks to add to your rotation.
Let’s get into them.
‘Bridget Jone’s Diary’ (2001)
Bridget Jones and her hilarious love stories, mishaps and entanglements have continued entertaining us for decades. Told through diary entries, audiences fall in love with Bridget as she faces the trials and tribulations of trying to improve oneself.
And with sequels including Bridget Jones: The Edge of Reason and Bridget Jone’s Baby that are nearly as funny as the first, this series is a romantic comedy classic.
‘My Big Fat Greek Wedding’ (2002)
In this early aughts rom com, falling in love is easy. Getting the family on board? Now that’s a different story. When Toula falls in love with a non-Greek man, her traditional Greek family is not pleased. But Toula knows how she feels and proceeds to do whatever she can to open her family up to Ian.
An extremely heartwarming film, My Big Fat Greek Wedding explores themes of identity, culture and the pressure to conform we’ve all experienced at some point in life.
‘How to Lose a Guy in 10 Days’ (2003)
Kate Hudson and Matthew McConaughey. Enough said, right? Andy (Hudson) works as a magazine writer and wants to make it big. Ben (McConaughey) is an advertising exec who wants to win a big client.
Both of them are seemingly willing to do whatever it takes to get what they want, but what happens when the game gets more complicated than they ever expected?
‘Deliver Us From Eva’ (2003)
Eva Dandridge is a strong, independent woman who loves getting in the middle of her sisters’ love lives. One thing she isn’t interested in, however, is her own love life. When her sisters decide to take matter into their own hands and pay someone to start dating Eva, all bets are off.
In addition to the humor and romance throughout the film, the family dynamics between the sisters is yet another reason to watch this romantic comedy.
’13 Going on 30′ (2004)
When 13-year-old, Jenna Rink, makes a wish to be “30 and flirty and thriving,” that’s exactly what she gets, or so she thinks. After waking up in her 30-year-old body, Jenna (played by Jennifer Garner) finds herself living the dream: a fancy apartment, a gorgeous boyfriend and a stellar job as a magazine editor.
What she quickly realizes, though, is that her life isn’t what she expected it to be, and she’s the only one who can fix it.
‘Hitch’ (2005)
Alex “Hitch” Hitchens (Will Smith) is the best dating coach out there, with a playbook filled to the brim to help awkward men woo their dream woman to find their happily ever after. Sara Meleas (Eva Mendes), a cynical gossip columnist, is seemingly immune to Hitch and his moves.
With a creative plot and tons of funny moments, Hitch is certainly another classic rom com to add to your list.
‘Fever Pitch’ (2005)
Drew Barrymore and Jimmy Fallon star in this classic romantic comedy set in the iconic city of Boston. When Ben, a schoolteacher obsessed with the Boston Red Sox, and Lindsey, a corporate exec, meet, they don’t think much about the vast differences between them.
When those differences become too big to ignore, however, the couple must determine if their feelings for each other are enough to make it work.
‘She’s the Man’ (2006)
Amanda Bynes brings her signature comedic charm to this modern twist on Twelfth Night. When Viola’s (Bynes) soccer team gets cut, she disguises herself as her twin brother to prove she can compete with the boys. But things get complicated when she falls for her new roommate, Duke (Channing Tatum), and a love triangle (or square) ensues. With fast-paced humor and over-the-top antics, She’s the Man is a 2000s rom com classic.
‘Failure to Launch’ (2006)
Matthew McConaughey and Sarah Jessica Parker star in this hilarious take on the man-child phenomenon. Tripp (McConaughey) is a 30-something who still lives with his parents—until they hire Paula (Parker), a professional motivator, to give him the push he needs to move out.
But when their fake relationship turns into something real, Tripp may have to grow up faster than he expected.
‘Definitely, Maybe’ (2008)
With a star-studded cast made up of Ryan Reynolds, Abigail Breslin, Isla Fisher, Elizabeth Banks and more, Definitely, Maybe is a seriously underrated rom com from the 2000s. When 10-year-old Maya (Breslin) asks her dad how her parents met, Will (Reynolds) tells her the story, but with a twist.
Throughout the film, both Maya and the audience are left guessing the real identities of the women in Will’s story, adding an element of surprise that will get you every time you watch.
‘Made of Honor’ (2008)
Best friends Tom (Patrick Dempsey) and Hannah (Michelle Monaghan) have been inseparable for years, but just as Tom realizes he’s in love with her, she announces her engagement to another man — a wealthy Scotsman, in fact.
Asked to be her maid of honor, Tom embarks on a last-ditch mission to prove he’s the one she should be walking down the aisle toward. A romantic comedy packed with friendship, grand gestures and a race against time.
’27 Dresses’ (2008)
Always a bridesmaid, never a bride. That’s the life that Jane Nichols (Katherine Heigl) has been living since all her friends started getting married. And to make matters worse, her younger sister is now getting married to the man Jane has secretly loved for years.
With a little help from Kevin, a cynical writer who doesn’t believe in marriage, will Jane finally be able to let loose and truly be herself?
‘Mamma Mia! (2008)
Set against the stunning backdrop of a Greek island, this feel-good musical follows Sophie (Amanda Seyfried) as she secretly invites three men—each a potential father—to her wedding in hopes of uncovering the truth about her parentage. With her free-spirited mother, Donna (Meryl Streep), caught off guard and the ABBA-fueled chaos that follows, Mamma Mia! delivers romance, laughter and pure joy in every scene.
‘He’s Just Not That into You’ (2009)
With an all-star ensemble cast including Jennifer Aniston, Drew Barrymore and Bradley Cooper, this rom com explores the highs and lows of modern dating through interconnected stories. As a group of Baltimore singles navigate love, heartbreak, and mixed signals, they’re forced to face the simple truth—sometimes, the signs are there, but we just don’t want to see them.
‘The Ugly Truth’ (2009)
Katherine Heigl and Gerard Butler bring the sparks in this battle-of-the-sexes rom com. Abby (Heigl), a type-A TV producer, is forced to work with Mike (Butler), a crass but charming dating expert who believes love is all about primal instincts. As they clash over seemingly everything, an unexpected experiment in love proves that sometimes, opposites really do attract.
‘500 Days of Summer’ (2009)
This unconventional romantic dramedy flips the classic love story on its head. When Tom (Joseph Gordon-Levitt), a hopeless romantic, falls for Summer (Zooey Deschanel), a free-spirited realist, he believes she’s “the one.”
But as their relationship unfolds through a nonlinear timeline, Tom is forced to confront the harsh reality of love, expectations and heartbreak in a way he never imagined.
‘The Proposal’ (2009)
Sandra Bullock and Ryan Reynolds star in The Proposal, a perfect blend of romance and comedy to watch over and over again. On the verge of deportation, no-nonsense executive, Margaret Tate (Bullock), convinces her assistant to marry her so that she can stay in the country. What follows is a journey to Andrew’s family’s home in Alaska, where the two find they may have more in common than they once thought.
And who doesn’t love the scene in the woods with the iconic Betty White? If you haven’t seen it yet, this is your sign to change that!
WATCH ROMANTIC COMEDIES & SO MUCH MORE WITH DIRECTV
These ten 2000s rom coms are some of the best of their time and are well worth rewatching for the first, second or tenth time. And the best part is, all of them are available to stream on DIRECTV, so all you have to do is press play and sit back and enjoy.
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Frequently Asked Questions
Why are 2000s romantic comedy movies so good?
Along with the nostalgia that comes with 2000s rom coms, these movies are so popular because of their relatable content around relationships, heartbreak, friendship and learning about who you truly are.
What are some of the best 2000s rom coms?
Fan favorite romantic comedies from the 2000s include '13 Going on 30,' 'How to Lose a Guy in 10 Days,' 'Cinderella Story' and '27 Dresses,' among so many others.
Which actors and actresses are in the most 2000s romantic comedy movies?
Popular rom com stars from the 2000s include Kate Hudson, Jennifer Lopez, Matthew McConaughey, Drew Barrymore, Adam Sandler, Will Smith and Cameron Diaz.
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