There’s nothing like a good 2000s rom-com to transport you back to an era of flip phones, butterfly clips, and impossibly grand romantic gestures. The golden age of chick flicks gave us swoon-worthy love stories, iconic fashion moments, and soundtracks that still live rent-free in our heads. If you’re craving a cozy movie night filled with nostalgia, here are some of our favorite throwback rom-coms from the 2000s that will never get old.
💛 How to Lose a Guy in 10 Days (2003)
Kate Hudson’s effortlessly cool Andie Anderson and Matthew McConaughey’s charming Ben Barry make this enemies-to-lovers story chef’s kiss perfection. Andie’s over-the-top tactics to “lose” Ben (hello, love fern and a very unfortunate rendition of “You’re So Vain”) combined with Ben’s secret bet to make her fall for him create the ultimate rom-com showdown. That yellow dress? Still iconic.
👗 27 Dresses (2008)
Katherine Heigl mastered the role of the ever-loyal bridesmaid, Jane, who has been in 27 weddings but never her own. Watching her go from self-sacrificing sister to finally putting herself first—while navigating her love-hate dynamic with James Marsden’s witty journalist—makes for the ultimate feel-good movie. The montage of all her dresses? A cinematic masterpiece.
💖 13 Going on 30 (2004)
Jenna Rink’s wish to be “thirty, flirty, and thriving” turns into a heartwarming (and hilarious) journey of self-discovery. From the “Thriller” dance scene to her adorable romance with Mark Ruffalo’s Matty, this movie is pure magic. It’s a reminder that growing up isn’t just about getting older—it’s about finding who you truly are.
🌺 50 First Dates (2004)
Drew Barrymore and Adam Sandler had rom-com chemistry down to a science in this quirky, heartwarming love story. Henry (Sandler) falls for Lucy (Barrymore), only to realize she has short-term memory loss and forgets him every morning. His daily attempts to make her fall in love with him all over again? Proof that true love never gives up.
👑 The Princess Diaries (2001)
A true comfort movie, The Princess Diaries gave us Anne Hathaway’s charmingly awkward Mia Thermopolis, who goes from high school outcast to actual royalty overnight. With Julie Andrews as the regal yet warmhearted Queen Clarisse, this movie is filled with girl-power moments, an unexpected glow-up, and that iconic foot-popping kiss.
💍 The Wedding Planner (2001)
Jennifer Lopez and Matthew McConaughey brought the ultimate wedding rom-com to life in this forbidden-love story. J.Lo’s perfectionist wedding planner, Mary, has everything under control—until she falls for the groom of her latest client. Between fairytale weddings and undeniable chemistry, this movie is peak early-2000s romance.
💔 He’s Just Not That Into You (2009)
An all-star ensemble cast (Jennifer Aniston, Bradley Cooper, Scarlett Johansson, and more) tackles modern dating struggles way before dating apps ruled our love lives. With multiple interwoven storylines, this movie perfectly captures the highs, lows, and very real realities of relationships—while still delivering all the charm and humor we love in a rom-com.
💕 Why We Still Love These Throwback Movies Today
Even in an era of instant messaging and dating apps, these 2000s rom-coms still feel as fresh and heartwarming as ever. Here’s why we keep coming back to them:
✨ Timeless Romance – Whether it’s slow-burn love (27 Dresses), childhood sweethearts (13 Going on 30), or serendipitous encounters (The Wedding Planner), these movies remind us that love stories—no matter how wild—never go out of style.
🎭 The Perfect Mix of Comedy and Heart – From Andie’s How to Lose a Guy in 10 Days antics to Mia’s royal transformation in The Princess Diaries, these movies make us laugh and tug at our heartstrings in equal measure.
👗 Unforgettable Fashion Moments – From Andie’s canary yellow dress to Jenna’s pink slip dress and fuzzy shrug, these films served major early 2000s fashion inspiration.
🎶 Iconic Soundtracks – You can’t hear “Love is a Battlefield” without picturing young Jenna dancing in her room or listen to “Somebody to Love” without thinking about Mia’s royal makeover. The music defined an era.
💌 Pure Nostalgia – There’s something comforting about revisiting these classics. They transport us back to a simpler time—before streaming algorithms and social media—when a good rom-com could instantly brighten your day.
