March 28, 2025

Early 2000s Romance Movies

Early 2000 romance movies just hit differently. I can’t put my finger on why exactly … Maybe it was because we were able to suspend disbelief before becoming jaded by the realities of our current toxic-productivity, chronically-online, dissecting-everything-to-death existence. Or maybe it was all the body glitter and the summer-fun, bop-filled, rom-com soundtracks.

Whatever the reason, they’re now a go-to comfort watch for so many of us. There’s no need to let go and move on. So, let’s get the popcorn bowl ready and kick back for a roundup of the best 2000 romance movies.

10 Things I Hate About You (1999)

Iconic, quippy and totally quotable, this modern Shakespeare adaptation belongs at the top of any early 2000s list (even though it’s technically on the cusp of the millennium). But Heath Ledger’s serenade? Julia Stiles’ poetry tear-jerker? Perfection.

Bring It On (2000)

This cheerleading classic highlighted the impressive acrobatics of the sport of cheerleading all while providing a sweet romance between Kirsten Dunst and Jesse Bradford. Also, spirit fingers.

A Knight’s Tale (2001)

Another Heath Ledger vehicle, this historical fantasy combined the excitement of medieval jousting with a contemporary soundtrack for maximum anachronistic fun.

Bridget Jones’ Diary (2001)

Jane Austen fans swooned for this Pride and Prejudice reimagining with Colin Firth reprising his role as Mr. Darcy, much to the delight of fans of the BBC series.

Legally Blonde (2001)

Elle Woods taught audiences that beauty and brains is always the best combination (and that the first cardinal rule of perm maintenance is that you’re forbidden to wet your hair for at least 24 hours after getting a perm at the risk of deactivating the ammonium thioglycolate). Throw in the incomparable Jennifer Coolidge for a film that warranted its sequels.

Sweet Home Alabama (2002)

Lightning never strikes twice and the parallels between Reese Witherspoon’s first and second romance is a testament to the anecdote. This romantic comedy makes us choose between a high-powered New York life and classic Southern charm.

Two Weeks Notice (2002)

A food-focused script has Sandra Bullock and Hugh Grant’s boss-assistant dynamic turn extra delicious. Fun, funny, and totally has us rooting for this pair.

My Big Fat Greek Wedding (2002)

A reaffirming watch for anyone who feels like the odd one out. This indie rom-com had us laughing about the awkwardness of love, family dynamics, and magic of Windex.

How to Lose a Guy in 10 Days (2003)

Cool girl archetype Kate Hudson takes Matthew McConaughey through the wringer in a battle of dating mind games—but even she can’t avoid their undeniable attraction and compatibility, so they end up falling for each other in the process.

Mean Girls (2004)

So fetch. The quintessential teen movie, timeless and still referenced and quoted twenty years later. This reliable rom-com was so successful it was adapted into a broadway musical, which then became a feature film as well.

13 Going on 30 (2004)

An incredible performance from Jennifer Garner has us truly believing a 13 year old is trapped inside her charming, adult body. Paired with Mark Ruffalo’s quiet sweetness, this one is oozing with nostalgia for the shared experience of our youth.