With Valentine’s Day just around the corner and February in full swing, there’s no better time to revisit some of the best rom-coms from the early 2000s. These films were made to make us laugh, swoon, and sometimes cringe in the best way possible. Whether you’re watching with a special someone or just in the mood for a feel-good flick, these 25 rom-coms will have you reminiscing about those unforgettable love stories that have stood the test of time. So grab your favorite snacks and get ready to take a trip down memory lane—it’s the perfect season for some classic romance!
1. 10 Things I Hate About You (1999) – Watch on Disney+
This one’s a modern take on The Taming of the Shrew. Heath Ledger and Julia Stiles bring the story to life in a way that’s funny, real, and easy to relate to. It's got that perfect mix of teen angst, humor, and a soundtrack you’ll still be vibing to.
2. Love & Basketball (2000) – Watch on HBO Max
A classic that shows love doesn’t always follow the rules. Sanaa Lathan and Omar Epps play childhood friends who realize their bond runs deeper than they thought. It’s got basketball, love, and those moments when you’re figuring it all out.
3. Bridget Jones's Diary (2001) – Watch on Amazon Prime Video
Renée Zellweger as Bridget is one of those characters you just get. She’s awkward, real, and totally lovable as she fumbles through her love life. It’s a good mix of laughs and a bit of "girl, same."
4. Brown Sugar (2002) – Watch on Hulu
If you love hip-hop and romance, this one's for you. Sanaa Lathan and Taye Diggs navigate their love for each other and for the culture. It’s smooth, relatable, and just feels right.
5. Notting Hill (1999) – Watch on Amazon Prime Video
Hugh Grant plays a bookstore owner who gets tangled up with Julia Roberts, a famous actress. It’s that classic “could this ever really happen?” story, but it’s charming, funny, and just feels like a feel-good classic.
6. The Best Man (1999) – Watch on Peacock
Taye Diggs, Nia Long, and the whole crew shine in this one. A wedding brings old friends back together, but there’s more going on beneath the surface. It’s funny, messy, and real about love, loyalty, and friendship.
7. 50 First Dates (2004) – Watch on Netflix
Adam Sandler and Drew Barrymore are an unlikely but perfect pair in this rom-com. Every day is a new start for Drew’s character, so Adam’s got to win her heart all over again. It’s sweet, funny, and surprisingly touching.
8. My Big Fat Greek Wedding (2002) – Watch on Amazon Prime Video
It’s not just a love story, it’s about family, culture, and figuring out how two different worlds come together. This one’s quirky and funny, with plenty of heart and those “wait, I get that” moments.
9. Why Did I Get Married? (2007) – Watch on Amazon Prime Video
Tyler Perry’s film is about relationships, truth, and how complicated love can get. The cast is strong, and it’s definitely one of those movies that has you thinking about your own life and choices while laughing at the same time.
10. Legally Blonde (2001) – Watch on Hulu
Elle Woods is more than just a sorority girl trying to win back her ex. She goes to Harvard Law, kicks butt, and learns a lot about herself in the process. It’s funny, empowering, and feels good to watch.
11. Deliver Us from Eva (2003) – Watch on Hulu
Gabrielle Union’s character is no joke—she’s tough and protective of her family. LL Cool J’s character has to find a way into her heart, which isn’t easy. It’s a funny, sweet movie about breaking down walls and letting love in.
12. Love Actually (2003) – Watch on Peacock
A holiday classic that touches on love in all its forms—romantic, familial, and even the love that’s unspoken. It’s emotional, funny, and just the kind of movie you throw on when you want to feel all the feels.
13. A Lot Like Love (2005) – Watch on Amazon Prime Video
Ashton Kutcher and Amanda Peet show us that love isn’t always a straight line. It takes time, it’s messy, but it’s real. It’s one of those films that’s sweet without trying too hard.
14. Raising Helen (2004) – Watch on Amazon Prime Video
Kate Hudson takes on the role of a woman who unexpectedly becomes the guardian of her late sister’s kids. It’s a great mix of family drama, humor, and love. It’ll hit you in all the right places.
15. When Harry Met Sally... (1989) – Watch on HBO Max
This one's an all-time classic about whether men and women can just be friends. Meg Ryan and Billy Crystal have that perfect chemistry that makes you question everything you thought you knew about relationships.
16. How to Lose a Guy in 10 Days (2003) – Watch on Amazon Prime Video
Kate Hudson and Matthew McConaughey star in this rom-com where they try to win each other over while secretly sabotaging their efforts. It’s light, funny, and has great chemistry between the leads.
17. The Wedding Planner (2001) – Watch on Amazon Prime Video
Jennifer Lopez plays a wedding planner who falls for the groom (Matthew McConaughey). It’s cute, romantic, and has that mix of tension and humor that makes you root for the couple.
18. Think Like a Man (2012) – Watch on Amazon Prime Video
Based on Steve Harvey’s book, this rom-com dives into the games men and women play in relationships. With an all-star black cast, it’s funny, relatable, and gets into the real talk about love and relationships.
19. The Proposal (2009) – Watch on Hulu
Sandra Bullock and Ryan Reynolds have fantastic chemistry in this rom-com about a fake marriage turning into something real. It’s funny, awkward, and perfect for a feel-good movie night.
20. Something’s Gotta Give (2003) – Watch on Amazon Prime Video
Jack Nicholson and Diane Keaton explore love in later life, with plenty of laughs and emotional depth. It’s a funny and touching look at finding love when you least expect it.
21. Kate & Leopold (2001) – Watch on Amazon Prime Video
Hugh Jackman and Meg Ryan star in this sweet, funny, and charming love story that mixes time travel with romance. It’s a unique twist on the usual rom-com formula.
22. Fever Pitch (2005) – Watch on Amazon Prime Video
Drew Barrymore and Jimmy Fallon bring the laughs in this rom-com about balancing love with Fallon’s obsession with baseball. It’s funny, lighthearted, and a bit different from your usual romance flick.
23. Brown Sugar (2002) – Watch on Hulu
This one’s all about love, friendship, and hip-hop culture. Sanaa Lathan and Taye Diggs star in this beautiful, nostalgic movie about how music and love are intertwined.
24. Along Came Polly (2004) – Watch on HBO Max
Ben Stiller and Jennifer Aniston show how opposites attract in this quirky, sweet movie about a guy recovering from heartbreak while falling for a free-spirited woman.
25. The Wedding Singer (1998) – Watch on Netflix
Adam Sandler and Drew Barrymore bring the laughs in this '80s nostalgia-filled rom-com. It’s funny, sweet, and all about second chances when it comes to love.
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