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Ah, the 2000s—a decade of butterfly clips, tank tops over T-shirts, and rom-coms that knew how to make us laugh, cry, and believe in love again (with an iconic pop soundtrack, of course). In an era before dating apps and TikTok soft launches, romantic comedies ruled the box office with heart, humor, and just the right amount of chaos. These films weren't just a genre; they were a vibe—a comforting, sparkly hug we didn’t know we’d miss so much.
13 Going On 30
Part fairy tale, part coming-of-age story, 13 Going On 30 is the rare rom-com with heart and a moral compass. Jennifer Garner’s charm as a 13-year-old suddenly living in her 30-year-old body is timeless. The glittery nostalgia, the Thriller dance scene, and Mark Ruffalo’s shy-boy-next-door energy? Chef’s kiss.
13 GOING ON 30 [2004] – Official Trailer (HD), Sony Pictures Entertainment
27 Dresses
Katherine Heigl carried the early 2000s rom-com scene on her well-dressed shoulders, and 27 Dresses is her crowning jewel. The ultimate tale of being the always-a-bridesmaid, never-the-bride, it features unforgettable one-liners, wedding montages galore, and James Marsden’s smirky charm.
27 Dresses (2/5) Movie CLIP - All 27 Dresses (2008) HD, Movieclips
50 First Dates
Drew Barrymore and Adam Sandler were the ultimate feel-good pairing in this sweet, offbeat love story set in Hawaii. Sure, the premise of dating someone with memory loss every day walks the line of problematic, but somehow 50 First Dates makes it wholesome. The tropical setting, Sandler’s sincerity, and the pineapple-slathered soundtrack make it ripe for a reboot.
50 FIRST DATES | Best Moments | Clips | Drew Barrymore, Adam Sandler, Ms. Movies by FilmIsNow
(500) Days Of Summer
Yes, it’s not a love story—it’s a story about love. And for that, (500) Days Of Summer remains a painfully accurate, emotionally raw, and stylistically cool entry in the rom-com canon. Joseph Gordon-Levitt’s crushed idealist and Zooey Deschanel’s manic-pixie heartbreaker still feel relevant in today’s commitment-phobic culture.
500 DAYS OF SUMMER | Official Trailer | FOX Searchlight, SearchlightPictures
Bridget Jones’s Diary
It’s rare that a movie can make you feel secondhand embarrassment, joy, and empowerment all at once, but Bridget pulls it off. With her bunny costume mishap, her drunken escapades, and two men literally fighting over her in the street, Bridget Jones is the chaotic queen we all still relate to.
Mark Reads Bridget's Diary - Bridget Jones's Diary | RomComs, RomComs
Brown Sugar
Romance and hip-hop? Name a more iconic combo. Brown Sugar gave us a love story wrapped in beats and bars, starring Sanaa Lathan and Taye Diggs with chemistry that practically sizzled off the screen. It was smart, sexy, and culturally rich—everything a rom-com should aspire to be. This is one that deserves a reboot and a deluxe vinyl soundtrack rerelease.
A Cinderella Story
Is it even the early 2000s without Hilary Duff in a low-rise skirt and a flip phone? A Cinderella Story gave the classic fairy tale a Y2K makeover, complete with football player Prince Charmings, diner uniforms, and the iconic line: “Waiting for you is like waiting for rain in this drought". Snaps. Let’s give it a gritty-but-adorable modern update. TikTok dances optional.
Deliver Us From Eva
Underrated doesn’t even begin to cover it. Deliver Us From Eva gave us a whip-smart, no-nonsense Gabrielle Union and a smooth-talking LL Cool J in a plot that mashes Taming of the Shrew with early 2000s sass. It was slick, sexy, and brimming with chemistry. In an era finally appreciating strong Black leads in romance, this one deserves a rewatch and a revival.
Deliver Us from Eva | Gabrielle Union’s Scary Health Inspection, Universal Pictures
Enchanted
Not just a rom-com, Enchanted was a genre-bender that brought Disney animation to real life—and gave us Amy Adams at her most charming. It poked fun at fairy tales while delivering one of the best of them. With a sequel (Disenchanted) already in the books, we say: reboot the magic, not just the movie. Bring Giselle back in a multiverse of princesses or a musical miniseries.
Enchanted - 2007 Theatrical Trailer #1 (May 22, 2007), Animation Compendia
Hitch
Will Smith as a dating coach with a secret sensitive side? Sold. Hitch was equal parts suave and slapstick, with just enough life advice to make you believe your next Hinge match could be The One. With dating culture getting weirder by the day (hello, voice note flirtations), this one is screaming for a Gen Z reimagining.
Hitch (2005) Official Trailer 1 - Will Smith Movie, Rotten Tomatoes Classic Trailers
How To Lose A Guy In 10 Days
Kate Hudson’s yellow dress. Matthew McConaughey’s “frost yourself.” The plant named love fern. This movie was iconic before the word iconic became overused. It’s the ultimate battle-of-the-sexes rom-com, wrapped in glossy magazine chaos and fake-dating hijinks. Let’s reboot it with reversed roles and watch the love fern bloom all over again.
How to Lose a Guy in 10 Days (1/10) Movie CLIP - How It's Done (2003) HD, Movieclips
Last Holiday
Queen Latifah discovers she’s dying and decides to live—cue the luxury European hotel, gourmet meals, and LL Cool J falling for her. This movie is a sweet reminder to seize the day (and buy the fancy dress). Wholesome and quietly radical, Last Holiday still feels ahead of its time. We need more rom-coms about joy, indulgence, and late bloomers.
Last Holiday (1/9) Movie CLIP - Three Weeks to Live (2006) HD, Movieclips
Love Actually
It’s not just a Christmas movie—it’s a state of mind. Love Actually manages to be cheesy and heartwarming with just enough British sarcasm to keep it grounded. While we got a mini-sequel of sorts in 2017, we’re due for an update. Where are those characters now? Does Sam still play the drums? Did Juliet ever realize that video montage was weird? Let’s find out.
Love Actually | Official Trailer | Re-releasing In Cinemas November 24, Universal Pictures UK
Maid In Manhattan
J.Lo in a white trench coat walking through a luxury hotel lobby like she owns it? Yes, please. Maid In Manhattan gave us class-clashing romance, single-mom struggles, and Ralph Fiennes inexplicably falling for someone while barely knowing her. It’s a fantasy—but one we still want to believe in. Time to bring back the rags-to-riches romance with a modern immigrant twist.
MAID IN MANHATTAN [2002] – Official Trailer (HD), Sony Pictures Entertainment
My Big Fat Greek Wedding
A cultural reset. My Big Fat Greek Wedding is still the highest-grossing rom-com of all time for good reason—it’s heartfelt, hilarious, and full of family chaos. With the third film released in 2023, we say: let this become the Fast & Furious of rom-com franchises. Give us My Big Fat Greek Retirement, My Big Fat Greek Divorce (and reunion!), and everything in between.
My Big Fat Greek Wedding (2002), Hailey Ivan-Hodges
The Princess Diaries 2
Sure, it’s technically a royal coming-of-age story—but the Anne Hathaway-Chris Pine flirtation? Peak rom-com energy. The Princess Diaries 2 brought tiaras, spontaneous musical numbers, and Julie Andrews singing. We never got a third film, and frankly, that's a cinematic injustice. Let’s go back to Genovia already.
The Princess Diaries 2: Royal Engagement - Official Trailer (2004), The Julie Andrews Archive
She’s The Man
Amanda Bynes as a soccer-playing teen disguised as her brother? Shakespeare never felt so sporty. She’s The Man is chaotic, quotable, and genuinely hilarious. (“I like cheese.”) With gender roles and fluidity more openly discussed now, a reboot could add layers of depth—and still keep the laughs. Game on.
She's the Man (2006) Trailer #1 | Movieclips Classic Trailers, Rotten Tomatoes Classic Trailers
The Wedding Planner
J.Lo again (queen of the 2000s!) and Matthew McConaughey fall in love while planning his wedding to someone else. Scandalous! The Wedding Planner is glossy, ridiculous, and exactly what you want when you’re feeling hopelessly single. It could easily be reimagined for a post-Pinterest world—complete with influencer weddings and unrealistic Pinterest boards.
THE WEDDING PLANNER [2001] - Official Trailer (HD), Sony Pictures Entertainment
Two Weeks Notice
Sandra Bullock and Hugh Grant? Say less. Two Weeks Notice pairs a neurotic, mission-driven lawyer with a charming billionaire man-baby, and somehow it works. It's snappy, quippy, and oddly prescient about burnout and boundaries. The workplace rom-com needs a comeback—and Lucy Kelson should be leading it.
Two Weeks Notice (5/6) Movie CLIP - What Baby? (2002) HD, Movieclips
The Sweetest Thing
This chaotic, raunchy, NSFW gem starred Cameron Diaz, Christina Applegate, and Selma Blair before women being messy on screen was trendy. It was wild, unapologetic, and full of quotes you probably shouldn’t say in front of your boss. A revival would totally work today—especially with its positive, sisterhood-first messaging.
THE SWEETEST THING [2002] - Official Trailer (HD), Sony Pictures Entertainment
Sweet Home Alabama
“You can have roots and wings”. Reese Witherspoon’s rom-com about going home, growing up, and choosing between a diamond heir and a high school sweetheart still makes us swoon. It’s Southern charm meets New York ambition—and with Witherspoon back in the rom-com saddle, now is the perfect time for Melanie’s next chapter.
Sweet Home Alabama movie, Jake and Mel, Marina Capri
Something’s Gotta Give
Romance doesn’t stop at 30—or even 60—and Something’s Gotta Give proves it. Diane Keaton and Jack Nicholson are a refreshingly mature pair navigating love later in life, with coastal real estate porn and Nora Ephron-style dialogue to boot. With a current appetite for “silver fox” love stories (hi, The Golden Bachelor), this one’s begging for a follow-up.
Something's Gotta Give | Erica's Most Relatable Moments | Love Love, Love Love
Final Thoughts
These 2000s rom-coms weren’t just funny or flirty—they shaped an entire generation’s idea of love, self-worth, and what it means to walk in slow motion to a killer soundtrack. If Hollywood’s looking for magic again, they don’t need to look far. Just dust off the flip phones, bring back the meet-cutes, and let the love (and sequels) flow.
Something's Gotta Give | Erica's Most Relatable Moments | Love Love, Love Love
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