Love is in the air, and there’s nothing better than a good rom-com to settle on. Whether it’s a makeover montage, a grand romantic gesture, or a witty best friend stealing the scene, the early 2000s gave us some of the most iconic rom-coms thus far. If you’re looking to dive into a little nostalgia and a lot of heart, here are some of the best early 2000s rom-coms you need to rewatch.
13 Going On 30, released in 2004, is everything a rom-com should be– funny, heartfelt, and packed with just the right amount of humor. Jenna Rink’s magical journey takes us from an awkward preteen to a glamorous 30-year-old, until she finds out adulthood has its challenges. Despite all the ups and downs of being an adult, Jenna reunites with her childhood best friend and neighbor, Matt. As Jenna navigates the complexities of her new life, Matt helps her understand what truly matters– love, friendship, and being true to herself. Their bond grows stronger, and in the end, their love story reminds us that sometimes the best relationships are built on a foundation of years of friendship and understanding.
10 Things I Hate About You, released in 1999 and inspired by Shakespeare’s The Taming of the Shrew, embodies the classic enemies-to-lovers trope. When the infamous Patrick Verona gets paid to date Kat Stratford, falling for her is the last thing on his mind. However, as Patrick spends more time with Kat, her fierce independence and sharp wit win over him, and what started as a sharp banter evolves into a genuine connection. With unforgettable scenes like Patrick’s stadium performance and Kat’s heartfelt poem, the movie perfectly balances humor and sincere moments. The chemistry between Kat and Patrick is unmatched, making their love story feel genuine and everlasting.
27 Dresses, released in 2008, is the ultimate “he fell first, she fell harder” rom-com that perfectly captures the charm of unrequited love. Jane Nicholas, a perpetual bridesmaid to many, has spent her entire life putting others first, especially her younger sister, who unexpectedly gets engaged to Jane’s longtime crush, her boss. Kevin Doyle, a wedding writer, sees Jane’s story as his next big article but soon finds himself drawn to her presence. With the help of Kevin, Jane learns to prioritize her happiness, despite the initial back-and-forth bickering, ultimately transforming into undeniable chemistry. With iconic moments like the bar singalong, 27 Dresses is a heartfelt movie that proves love can find you when you least expect it.
How to Lose a Guy in 10 Days, released in 2003, is a classic romcom with an unforgettable story. Andie Anderson, a journalist hoping to write an article on dating mistakes, sets out to drive a man away in ten days, as suggested by the title. At the same time, Ben Barry, an advertising director, makes a bet that he can make any woman fall in love with him within the same timeframe. As the two try to outdo each other, what starts as a game quickly transforms into real feelings. Kate Hudson and Matthew McConaughey deliver an iconic performance, serving up charm, chaos, and chemistry– everything a romcom should be. If witty banter, undeniable chemistry, and a love story that sneaks up on you are things you enjoy, this is a must-watch.
She’s the Man, released in 2006, is a hilarious rom-com inspired by Shakespeare’s Twelfth Night. When Viola Hastings is denied the chance to play on her school’s boy’s soccer team, she disguises herself as her twin brother, Sebastian, and enrolls at his new school to prove her skills. What starts as a simple plan turns chaotic when she develops feelings for her roommate and soccer captain, Duke Orsino, who is crushing on Olivia, a girl who has feelings for “Sebastian.” With comedic misunderstandings, witty dialogue, and Amanda Bynes’ memorable performance, She’s the Man delivers messages about both romance and breaking gender stereotypes.
To All The Boys I Loved Before, although not released in the early 2000s, is just as magical as the rest. When 11th grader Lara Jean’s hidden love letters get mailed to their recipients, her carefully managed life is thrown into chaos. To avoid an awkward confrontation with one of her recipients, Josh, who also happens to be her sister’s ex, Lara Jean starts a deal with Peter Kavinsky, another letter recipient, to fake a date. Unlike Lara Jean, Peter’s motive is to make his ex, Gen, jealous. As they navigate their staged romance, real feelings begin to develop. Despite Gen’s efforts to bring Lara Jean down, Peter is always there to assure her that she’s what he wants. The film highlights how opening up to someone can lead to genuine connection, and that love requires courage, honesty, and a willingness to step outside of our comfort zones.
