8 Cheesy 2000s Rom-Coms We Can’t Stop Rewatching
When the world is burning, and everything is garbage, cheesy rom-coms are the perfect melody. Ridiculously joyful but also brimming with all-encompassing depictions of adoration, with some wildly absurd scenarios that may not be possible in the real world? Frankly, I'll take them all. The 2000s were also full of some of the best cheesy rom-coms, and we have yet to replicate their greatness. Despite many critics calling them flops, they're perpetual winners in my book and will always be.
From the Christmas gem, The Holiday (2006), to the underrated treasure, Penelope (2007), here are some of the cheesiest rom-coms we love to rewatch for comfort, as well as where you can stream them on platforms like Prime Video and more.
The Holiday is a national treasure and a love letter to moviemaking in the most delightful way. Full stop. It's probably a large reason why we're all so obsessed with the cottagecore aesthetic, too. Plus, Jude Law as a nerdy single dad. Need I say more? The concept of a movie like The Holiday simply wouldn't happen in real life because we've all got way too many trust issues to lend our house to a stranger on some site.
Still, it's one of the most comforting Christmas movies with two romances that are both equally compelling and lovely. If you're in the mood for a fast burn with some of the best tropes and found family vibes, this cozy classic holds up beautifully.
While many people know Chris Evans for his embodiment of Captain America in the MCU, he's one of the few actors who can also be deemed a rom-com king. Viewers recently fell in love with him after his stunning monologue in Materialists (2025), but What's Your Number? will always be Evans' best. He and Anna Faris make a perfect team as neighbors-to-friends-to-lovers, and all their interactions are glorious.
Perfect for anyone who loves ridiculous occurrences and easy banter coupled with a natural slow-ish burn, What's Your Number? delivers in spades. Given its time period, it also features cameos from other actors who've been in the MCU, so it's an overall delight when it comes to the casting. More than that, it's a swoonworthy rom-com with Evans getting to sing. I don't need to say more, do I?
When it comes to 27 Dresses, it's all about the last line. If you know, you know. It's something I think about so often, and it's the pinnacle of what romance should be. But the movie is also an absolute blast, even if it's ridiculous, because, genuinely, why would a woman keep all 27 of the bridesmaids' dresses she owns? Perfect for anyone who loves wedding-centered stories like Made of Honor (2008), 27 Dresses hits like catnip with the way that Jane and Kevin get together.
It plays with some of the best tropes and involves the most understandable type of miscommunication and forced proximity on the job that leads to them falling for each other. Plus, a cynical writer writing about love who's also a secret softie? James Marsden brings his A-game in this one, and you'll never listen to Elton John's "Bennie and the Jets" the same way.
Like The Holiday, Serendipity is a Christmas staple, but an underrated one at that. While the film only starts around the holidays, like While You Were Sleeping (1995), it has all the cozy New York winter vibes to make it a must-watch this time of year. And while the narrative is ultimately wildly far-fetched in order to honor the title of the movie, it's the kind of cheesy that genuinely makes you believe destiny has a sweeping sense of humor.
John Cusack and Kate Beckinsale make an adorable team, and how the two meet, then find their way back to each other, makes me ugly cry every single time. If second chance romances are your bread and butter, but you've been somehow sleeping on this treasure, please rectify it immediately. It'll scratch all the right itches while delivering the type of precious romance we could always use more of.
I will never understand how fellow critics gave She's the Man such a low rating because no movie has ever made me laugh harder. Plus, for the early 2000s, it was surprisingly progressive, which says something considering it's based on Shakespeare's Twelfth Night.
Amanda Bynes is an absolute legend in the movie, and how she brings Viola and Sebastian to life is genuinely hysterical. It's totally absurd that they didn't get caught earlier, but I'm willing to suspend disbelief for how many hilarious lines it's given us that some of us can still quote to this day. Perfect for anyone who wants the comedy to be loud in the rom-com, this one's still a banger with a romantic arc that'll still make you swoon.
Another underrated gem that way too many people sleep on is Chasing Liberty—five words: Matthew Goode on a motorcycle (vespa-ish). If you can't help but swoon every time Patrick Verona steps onto the screen in 10 Things I Hate About You (1999), then Chasing Liberty is the movie for you. It's also for the girlies who grew up loving My Date With the President's Daughter (1998).
But that's not all, the hidden identity in Chasing Liberty makes it extra delicious and angsty, delivering the kind of payoff that's truly chef's kiss. When it comes to Mandy Moore movies, few things top the perfection of Chasing Liberty. Full of wild adventures and a believably angsty romance, there are also a ton of parallels to Tangled (2010), which make it even more delightful to watch if you're also a fan of the story.
Like Serendipity and Chasing Liberty, Penelope is another underrated gem that too many people are sleeping on. With a mix of fantasy into the narrative, it's the type of romance for people who want a sprinkle of magical realism in their rom-coms. Starring Christina Ricci, James McAvoy, and the late and sensational Catherine O'Hara, everything about Penelope should've resulted in a bigger hit.
It's hilarious and fun throughout, deeply heartwarming, and beautifully soft by the end in a way that'll evoke all the giddy emotions. McAvoy is guaranteed to make you swoon, Ricci is so precious, and it's also the kind of cozy romance that's perfect for the fall season, so there's a bonus. As wild as it is, there's also a warmth throughout that's impossible to describe.
At times, He's Just Not That Into You will drive you absolutely mad with some of the foolish stereotypes and dated conversations, but there's something still ridiculously cozy, and in large part, it's because of the ensemble cast. Stories like this don't always work with different romances scattered throughout, but oddly, He's Just Not That Into You does. It feels authentic, which is why you stick with it to the end, no matter how frustrating the characters are.
Of all the movies on this list, this one genuinely feels like the cheesiest, yet that's precisely part of its charm. Matters within the film shouldn't work out the way that they do in the real world, but the execution in the movie ensures that the love stories feel earned. Most importantly, Justin Long's character alone is worth watching the movie for.
