10 Classic 2000s Rom Coms to Watch (or Rewatch) Any Time

10 Classic 2000s Rom Coms to Watch (or Rewatch) Any Time

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 2000s rom coms to watch (or rewatch) won’t disappoint.

And the best part is, you can watch or stream them all on DIRECTV today!


On this list you’ll find a variety of rom coms to choose from the early 2000s up until the start of the 2010s. And while some of these you’ve almost certainly watched before, this list will hopefully give you a few new flicks to add to your rotation.

Let’s get into them.

‘Bridget Jone’s Diary’ (2001)Bridget Jones Rom Com Poster

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.

Watch Bridget Jones’s Diary Full Movie on DIRECTV

‘My Big Fat Greek Wedding’ (2002)My Big Fat Greek Wedding movie poster

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.

Watch My Big Fat Greek Wedding Full Movie on DIRECTV

‘How to Lose a Guy in 10 Days’ (2003)How to Lose a Guy in 10 Days Movie Poster

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?

Watch How to Lose a Guy in 10 Days Full Movie on DIRECTV

‘Deliver Us From Eva’ (2003)Deliver_us_from_eva_poster.jpg

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.

Watch Deliver Us From Eva Full Movie on DIRECTV

’13 Going on 30′ (2004)13 Going on 30 movie poster

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.

Watch 13 Going on 30 Full Movie on DIRECTV

‘Hitch’ (2005)Hitch romantic comedy poster

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.

Watch Hitch Full Movie on DIRECTV

‘Fever Pitch’ (2005)Fever Pitch movie poster

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.

Watch Fever Pitch Full Movie on DIRECTV

‘Definitely, Maybe’ (2008)definitely, maybe 2000s movie poster

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.

Watch Definitely, Maybe Full Movie on DIRECTV

’27 Dresses’ (2008)27 Dresses Movie Poster

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?

Watch 27 Dresses Full Movie on DIRECTV

‘The Proposal’ (2009)The_Proposal_Movie_Poster_2000s

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 27 Dresses Full Movie on DIRECTV


These 10 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.

Share the love – and get paid! Refer friends & family to DIRECTV and everybody wins! DIRECTV customers connected via Satellite or via Internet can get up to $500 in eGift cards when someone they refer signs up for new service. ($100 per new customer)

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.

The content is featured on is editorial content brought to you by DIRECTV. While some of the programming discussed may now or in the future be available affiliates distribution services, the companies and persons discussed and depicted, and the authors and publishers of licensed content, are not necessarily associated with and do not necessarily endorse DIRECTV. When you click on ads on this site you may be taken to DIRECTV marketing pages that display advertising content. Content sponsored or co-created by programmers is identified as "Sponsored Content" or "Promoted Content."