As a twenty-something-year-old, rom-coms from the early 2000s basically shaped my very existence. Even though they all may follow the same formula (awkward boy/girl in search of love ➡️ sappy meet-cute ➡️ failed attempt at romantic trysts ➡️ picture-perfect kiss ➡️ movie fades while pop song plays), they are Hollywood staples.

Listen, I’ll be the first to say it, many of my favorite flicks have an undeniably cheesy plot, script, and acting, but that’s a rom-com for you, baby! The Pop Insider team had a HEATED discussion about the all-time best ’00s rom-coms, and things got a little cray. Our staff weighs in below.

Steph Grassullo (AKA me!): She’s the Man (2006)

This is Amanda Bynes in. her. PRIME.

The plot of the movie is… a bit farfetched, but it is based off of Shakespeare’s Twelfth Night, so that makes it OK, right? True to Shakespearean comedy, the film features scenarios that escalate to the craziest proportions. It’s the classic twin swap, except this time one siblings portrays her twin of the opposite sex. Classic. Skip to Amanda Bynes’ character being put in uncomfortable locker room situations, awkward dorm room setups, and falling HARD for her fellow teammate and roomie. 

Oh, and it also helps that Channing Tatum is shirtless for the majority of the movie. 10/10, will recommend. 

Jackie Breyer: 50 First Dates (2004)

B/c Drew Barrymore. I have always been obsessed with this angel of an actress. Barrymore is beautiful inside and out, and was a quintessential actress of the ’90s and ’00s. She and her co-star Adam Sandler have an easy-going, real-life friendship that makes their on-screen interactions seem natural and believable—even with Sandler’s over-the-top character acting. While the premise of 50 First Dates is somewhat unbelievable, Barrymore is the perfect actor to play the role. Her personality conveys a certain innocence or naivete that is both charming and fitting for the role.

Marissa DiBartolo: 13 Going on 30 (2004)

You mean, aside from Mark Ruffalo in the cutest role of all time? C’mon. He’s an adorable, artsy photographer with a scruffy face and an endless arsenal of faded band T-shirts and old Vans sneakers. I cannot. Be still my teenage heart.

This movie meant everything to me and still does (shoutout to E! for almost always playing this on the weekends). This absolute gem came out in 2004 when I was 14, so I really, really got it. I wanted to be 30, flirty, and thriving and end up with the boy next door who turned out to be super awesome. Jenna was also a journalist at a magazine, which is the only thing I’ve ever wanted to be. And Jennifer Garner in general is also just #goals. From dumping garbage friends, to making the choice to be the better person, to eating way too many Razzles, this movie inspired me on so many levels. 

Did I mention Mark Ruffalo?

Ali Mierzejewski: How to Lose a Guy in 10 Days (2003) 

This is a great film. Like most leading ladies in the early 2000s, Andi Anderson was a journalist at a magazine. She was living the New York dream. Ben Barry is trying to get ahead in his advertising firm by landing a big diamond account. Fun fact: He is also living the New York dream. It’s Kate Hudson and Matthew McConaughey, who are the most cool and chill people of all time, making their characters the most cool and chill of all time. (He rides a motorcycle! She watches basketball!)

The plot of this movie is classic Shakespearean comedy. She’s trying to find a guy to date and “lose” in 10 days. He’s trying to make a girl fall in love with him in the same amount of time. The supporting characters set up a romantic whirlwind of a plot where they meet each other and begin to date—trying to accomplish different things! WHAT A TALE. Also, they play bullsh*t in this movie, which is one of my favorite card games of all time.

Maddie MichalikA Cinderella Story (2004)

The plot of this movie is everything. We’ve got all we need to spin-off the classic Cinderella tale: A mean stepmother, two crazy stepsisters, and ONLY Sam has to work in the diner. It’s so unfair. But then, her and Austin become secret pen pals, but on a more technological level—on her Sprint flip phone—because paper is sooooo ‘90s. Austin is so blinded by love that he can’t tell who is behind the smallest masquerade mask ever made. Sam drops her cell at homecoming, and there’s a whole hunt to find out who Cinderella is.

“Do you believe in first sight?” “I’ll let you know.” is the most ICONIC exchange of all time, don’t @ me.

Xandra Harbet: Crossroads (2002) 

Queen Brit is the love of my life, need I say more? Okay, fine. I’ll say more. Britney Spears could star in a five hour movie dressed in a trash bag reading a dictionary and I would insist that it’s the best thing ever created. But, this movie wasn’t just awesome because of Brit. Even now, this movie is #relatable, probably even more so than when I saw it as a kid.

We all drift apart from our friends, especially when we’re younger, sometimes for the dumbest reasons. There are always those wistful thoughts in the back of your mind that you might reconnect, even though a lot of times, you know you’re better off without certain people in your life. This movie fills the nostalgia quota for reconnection without you having to actually do it yourself, because in real life it doesn’t usually tie up neatly in a bow.

Jacqueline Cucco: Win a Date with Tad Hamilton (2004)  

This movie was my teenage dream. Just a regular girl who wins a date with a super-famous, super-hottttt mega star actor, who happens to fall in love with her. Considering that my high school years consisted of stalking boy bands, relentlessly calling radio stations to win tickets to CD release parties, and sneaking backstage so I could meet them, this movie resonated with me big time.

Kelly Corbett: Employee of the Month (2006) 

Overall, I hate love movies because love is stupid and none of that sh*t happens IRL. Or it does briefly, and he leaves and all you have is your failing Tumblr to console you. Anyway, I was asked to give an answer since I work here, so I chose Employee of the Month because I thought Dane Cook looked good in this movie and was a lot better than the other guy and he lived with his Grandma and that’s cute AF. Whereas Dax Shepard is just annoying, so he doesn’t deserve Jessica Simpson. This was actually a comedy. I’m sorry, everything else makes me want to barf.

Katelyn Kearns: The Princess Diaries (2001)

It has everything my child self could dream of: A celebrity makeover, royal status, beautiful clothes, and some heartbreaking twists… I really would love those now, too.

The plot of the movie is dream-like: Mia finds out one day that her grandmother from Europe is actually the queen there… Making her royalty! The repercussions of this are sadly realistic, but luckily help Mia change for the better. From the San Francisco backdrop to the stunning mansion decor, the aesthetic is overall perfection. The end scene with her royal ball is everyone’s dream party. The humor is still the best in a rom-com I’ve ever seen, and it’s relatable, as we each have a Mia, a Queen Julie Clarisse, and a Joe inside us all.

About the author

Stephanie Grassullo

Stephanie Grassullo

Stephanie Grassullo is an associate editor at Adventure Publishing Group. In addition to handling toy and licensing news and updates for The Toy Book and The Licensing Book, Stephanie also writes toy reviews and commentaries for the Toy Insider. When she’s not binge-watching old episodes of Gossip Girl, Stephanie is always game for Boggle tournaments—she’s the titleholder Boggle champion in her family, and proud of it! Stephanie firmly believes that there is no awkward moment that can’t be remedied with the help of Bop It. To get to know her better, follow her on Twitter @steph_grass.