Top 10 Most Rewatched 2000s Rom-Com Moments

“A Cinderella Story” (2004)

There’s just something about the rain that makes a kiss that much more romantic. Maybe it’s the way both people so badly want to be with each other they don’t care about getting soaked, or maybe it’s the symbolism of washing away all past transgressions. Either way, the one from “A Cinderella Story” is extra special because of the payoff. Earlier in the movie, Sam compares waiting to Austin like waiting for rain in a drought. Well, wouldn’t you know it, the rain has finally arrived. Everything from the direction of the scene to Jimmy Eat World in the background makes this a picture-perfect moment.

“She’s the Man” (2006)

Although it’s hard to imagine Channing Tatum ever being shy and uncomfortable talking to girls, the sentiment is sweet. Viola, pretending to be her brother Sebastian, gives Duke some advice. It’s memorable for a few reasons. We get to hear Viola’s voice go up high, witness Duke’s bashfulness, and behold the ridiculousness that is the whole back-and-forth about cheese. Even though the girl persona she puts on doesn’t have a ton of chemistry with Duke, it’s obvious the real Viola and Duke do. Plus, the ensuing tarantula scene is peak humor.

“The Proposal” (2009)

When it comes to 2000s rom-coms there are few leading men who were as good at bringing both the rom and the com as Ryan Reynolds. He was at the height of his romantic and comedic powers in 2009’s “The Proposal” with Sandra Bullock. While his big, end of the movie proposal is definitely a romantic high note, it’s the terrible and hysterical duet that we keep coming back to. Whatever it takes to bond with your fake fiancée, right? Unfortunately for us, there’s no way we can ever hear the song again without thinking of this scene.

“Serendipity” (2001)

2001’s “Serendipity” is all about the idea of fate and the power that the smallest moments can have on our lives. Therefore, it kind of only makes sense that one of the biggest stand-out scenes is the movie’s very first. Fate and chance bring Jonathan Trager and Sara Thomas together for the first time, as they both grab for the last pair of black cashmere gloves in Bloomingdale’s. Between the well-written dialogue and soft smiles exchanged, we get a fantastic set-up and a scene we always stay to watch to the end.

“27 Dresses” (2008)

Getting song lyrics wrong is generally good for a laugh - just ask Phoebe Buffay and her version of Elton John’s “Tiny Dancer.” However, in “27 Dresses” Katherine Heigl and James Marsden’s characters take messing up lyrics to a whole other level. Again, it’s an Elton John song, but this time it’s “Bennie and the Jets.” What makes the scene so great - besides Heigl and Marsden’s chemistry and the entire bar joining in - is the duo’s completely wrong, yet totally awesome take on the lyrics. Lucky for them, the grammar police are much more common than the lyric police.

“The Holiday” (2006)

In a movie with two romantic storylines, one scene that always stands out doesn’t directly involve either of those romances. Rather, it’s the meeting of Iris, played by Kate Winslet, and Arthur, played by Eli Wallach. Their friendship begins when Iris sees Arthur looking confused and stops to give him a lift home. Arthur, being a former Hollywood movie writer, calls their coming together a “meet cute.” Discussing the term in a rom-com is wonderfully meta. For the true movie aficionados in the audience, the example Arthur gives is a reference to a scene from the 1938 film “Bluebeard’s Eighth Wife”, the first scene ever referenced as a “meet cute.”

“13 Going on 30” (2004)

Jenna getting ready for her first party as a 13-year-old in a 30-year-old’s body is full of joy and teenage glee. It’s like playing dress-up with your mom’s clothes, except they’re your clothes and you have the body to fill them out. As rewatchable as that moment will always be, it’s Jenna’s performance at the party that we will never get enough of. Surrounded by uptight, prim and proper adults, Jenna lets her inner child loose with the “Thriller” dance. She starts off alone on the dance floor, but in wonderful rom-com fashion, the room is eventually filled with zombie-dancing party goers.

“500 Days of Summer” (2009)

On day 34 of Tom and Summer’s relationship they head to IKEA. What begins as a simple trip to IKEA turns into one of the most sweetly comic moments of 2000s film. The new couple explore the different showrooms and adorably play house throughout the store. Not only is the scene incredibly rewatchable, it’s even permeated popular culture, making the idea of the ‘IKEA date’ an actual thing that people have started doing in the time since the film hit theaters. Word to the wise, if you’re going to do this, maybe just skip the bedroom part.

“Bridget Jones’s Diary” (2001)

If someone ever loves you enough to chase after you out in the snow wearing tiger skin print underwear, they’re probably the one. Bridget Jones does as much to win back Mark after he saw the awful things she wrote about him in her diary. The reveal that he isn’t angry with her, followed by that steamy kiss makes us melt every time. Even better, though, is the comment Bridget interrupts with and Mark’s perfect answer. We know it was snowing but, somehow, we doubt either of them were very cold in this moment.

Before we unveil our top pick, here are a few honorable mentions.

A Pregnant Charlotte Gives Big a Tongue Lashing Just before Her Water Breaks

The Confession to End All Confessions

Talk About Saying the Wrong Thing!

The Only Thing They’ve Ever Loved More Than Hip Hop Is Each Other

It Was a Great Line (Although, We Don’t Recommend Jumping on Moving Cars)

“Love Actually” (2003)

Not only is the cue card scene from “Love Actually” the most rewatched moment from 2000s rom-coms, it might just be the most imitated as well. The iconic scene has become a pop culture staple, with recreations and parodies being found throughout both television and movies in the intervening years. From Raj on “The Big Bang Theory” to Natalie in “Love Hard”, characters have been inspired plenty. “Saturday Night Live” even got in on the action a couple of times with very funny sketches. While we’re on the subject of “Love Actually” we also can’t forget Natalie’s adorably awkward and curse-filled first meeting with the new Prime Minister.