The Best 90s Early 2000s Rom-Coms to Stream for Your Next Movie Night with the Girls

POV: it’s Saturday night, you’re lounging on the couch with your best gal pals and you’re searching for an early 2000s rom-com movie to stream. Life is good.

As 90’s babies ourselves and growing up in the early 2000s, we know how special it was to grow up in the prime time of rom-com movies. With leading ladies being Julia Roberts, Jennifer Lopez, Kate Hudson and Meg Ryan, there’s no escaping the magic that filled the movie screen during this time.

It’s not too much to say that these movies molded the hopeless romantic in us. They made us cry, laugh and dream of finding our one someday. Now, over 20 years later, we still go back to these cozy, nostalgic movies time and time again. They are simply the best!

If you’re looking for the best 90’s early 2000’s rom-com movies for your next movie night with the girls, we’ve got you covered! We rounded up a list of our top 10 rom-coms to stream right now. Trust us, you’re going to want to bookmark this for later.

10 Best 90’s Early 2000s Rom-Com Movies

1. My Best Friend’s Wedding (1997)

My Best Friend’s Wedding goes down as our favorite rom-com of all time. 

It stars Julia Roberts, Durmot Mulroney and Cameron Diaz. The movie is about childhood friends, played by Julia Roberts and Durmot Mulroney, who make a pact to marry each other if they are both still single by 28. 

Days before his 28th birthday he announces that he’s going to marry. This then sends Julia Robert’s character, Julliane, into a tail spin after she realizes that she’s always been in love with him. She tries everything to stop the wedding, when things begin to get more complex.

2. The Proposal (2009)

We absolutely love The Proposal. If you’re looking for a light-hearted, comical movie with a twist of romance, this is a great movie to choose for a girls movie night.

The rom-com stars Sandra Bullock and Ryan Reynolds, who play the characters Margaret Tate and Andrew Paxton, respectively. Margaret is on thin ice when she realizes that she faces deportation back to Canada if something doesn’t change soon.

She quickly announces that she’s going to marry her assistant, Andrew Paxton, as a ploy to stay in country. Andrew agrees to go along with the act with the exception of Margaret going along with his own conditions. As they continue to run away from the truth, they are faced with some tangled feelings.

3. Maid in Manhattan (2002)

Jennifer Lopez is the queen of early 2000’s rom-coms and her character in Maid in Manhattan is possibly one of our favorites.

She plays a young single mom, who works as a maid in a five-star hotel in New York City. In a bout of crazy circumstances, her identity is mistaken for a high-profile celebrity. While mistaken for this celebrity, she meets a famous political heir.

They continue to grow feelings for each other, but when Marisa’s (Jennifer Lopez) true identity is revealed, their relationship takes a turn.

4. Monster-in-Law (2005)

Monster-in-Law stars Jennifer Lopez as well, and is such a funny movie to watch with friends.

It’ about a girl named Charlotte (Jennifer Lopez), who gets engaged to her boyfriend Dr. Kevin Fields (Michael Vartan). After meeting Kevin’s mom, she quickly realizes that her soon to be mother-in-law (Jane Fonda) is not happy to have a new person in the family. She tries everything to break up the wedding.

5. The Wedding Planner (2001)

The Wedding Planner is by far our favorite Jennifer Lopez rom-com to come out of the early 2000s. 

It stars Lopez (who plays Mary) and Matthew McConaughey (who plays Steve Eddison). In a crazy twist of fate, Mary stumbles upon meeting Steve and they instantly have chemistry with one another. However, Mary soon finds out that her job as a wedding planner quickly intertwines with Steve — creating a complicated situation for them both to figure out.

6. Sleepless in Seattle (1993)

Tom Hanks and Meg Ryan dominated the 90’s rom-com scene, and Sleepless in Seattle will forever go down as one of the best romantic comedies of all time.

The two stars play the characters Sam Baldwin and Annie Reed, respectively. After the death of Sam’s wife, his son calls into a radio show asking the host and the world to help find his dad a new wife.

Annie hears the radio show and falls in love with Sam. She then writes to him and asks him to meet her on the top of Empire State Building.

7. You’ve Got Mail (1998)

You’ve Got Mail is such a cozy rom-com movie. We love watching this movie on rainy days or when we’re needing a warm, light-hearted movie to boost our mood.

This movie also stars Tom Hanks (who plays Joe Fox) and Meg Ryan (who plays Kathleen Kelly).

Kathleen Kelly owns a boutique bookstore in Manhattan and can not stand Joe Fox — the owner of corporate, big-box book store who happens to have moved right across the street.

Ironically, they begin an intense, anonymous romantic relationship over IM. However, when Joe finds out who he’s really conversing with, he tries to resolve his mixed feelings for Kathleen.

8. 13 Going on 30 (2004)

13 Going on 30 is such a fun girly rom-com that will have you smiling from ear to ear and laughing all the way through.

The movie stars Jennifer Garner (who plays Christa Allen). The movie starts off with a teenager who wishes she had a boyfriend and a thriving adult. She soon finds herself waking up the next morning, nearly 20 years older and in the life she had dreamt of.

However, she soon discovers that finding love and juggling adult life is more of a challenge than she thought it would be.

9. 27 Dresses (2008)

When we’re looking for a girly, hopeless-romantic-type movie we always turn on 27 Dresses. Katherine Heigl is the leading role and absolutely shines.

Heigl plays the character Jane, who is a serial bridesmaid. She’s been in more weddings than she can count and dreams of one day having a wedding of her own. Jane soon finds out that her sister has fallen in love with her long-time friend, who she has been in love with her whole life.

Simultaneously, a reporter (played by James Marsden) is looking to write a piece about Jane, not knowing that it would change his life forever.

10. A Cinderella Story (2004)

If you grew up in the early 2000s, then you probably know the hold the love story between Hilary Duff and Chad Micheal Murray had on every young girl. A Cinderella Story will forever be one of the best, most nostalgic rom-coms of our childhood.

After Sam’s (Hilary Duff), father dies suddenly she’s left to live with her evil stepmother and twin sisters. As a teenager, she’s forced to work at the diner her dad used to own. Meanwhile, she starts an anonymous relationship with a boy via email.

They find out they go to school together and plan to meet at the the school masquerade dance. Sam soon finds out that the boy she’s been talking too is Austin Ames (Chad Micheal Murray), the most popular guy in school. She panics and drops her cell phone on the ground — leaving it in the hands of Austin to figure out who his mystery girl truly is.