14 Best Romantic Comedies from the 2000s

This was the decade that gave us Elle Woods, the “Date Doctor,” Bridget Jones, and Mia Thermopolis.

The romantic comedies of the early 2000s should get together and send a thank you note to their predecessors in the 90s. After all, the box office success of 90s rom-coms like My Best Friend’s Wedding and How Stella Got Her Groove Back paved the way for even more lovable rom-coms to be made in the early millennium.

From 2000 to 2010, Hollywood gifted us with laugh-out-loud storylines, charming female characters, and iconic fashion moments that will go down in film history. (Who didn’t fawn over Kate Hudson’s drop-dead-gorgeous canary yellow gown in How to Lose a Guy in 10 Days?)

From 13 Going on 30 to Hitch to Legally Blonde, there are so many delightful early 2000s rom-coms to indulge in. And while Hollywood is moving away (albeit slowly) from storylines solely about women whose lives revolve around romance — or panning women’s bodies up and down in a sexualized way with the camera — there are still plenty of cliché (but adorable) meet-cutes and romantic moments that can be appreciated in these films, even today.

Whether you want to relive those Friday nights at the movie theater or somehow missed these gems, discover our top 18 picks for the very best of the best in early aughts romantic comedies.

The Best Early 2000s Rom-Coms

How to Lose a Guy in 10 Days (2003)

If you can forget the fact that this fashion magazine’s sex and dating columnist, Andie Anderson (played by a dazzling Kate Hudson), is only 23, then you’ve got one of the most charming rom-coms to come out of the 2000s. Her latest assignment: Write about getting a guy (played by Matthew McConaughey) to fall for her and then dump her in just 10 days. The only catch: The hunky ad exec is trying to win a similar bet of his own. Who will come out on top?

Hitch (2005)

What if you could hire a “Date Doctor” to teach you how to fall in love? That’s the plot of this love story set against the backdrop of bustling New York City. Will Smith’s character, the incognito love counselor, helps his clients master the art of dating. But when a Page Six journalist, played by Eva Mendes, investigates who exactly Dr. Love is, she’s surprised to find out it’s the guy she’s falling for.

Bridget Jones’ Diary (2001)

Bridget Jones is living her 32-year-old single life in London. But she wants that single life to improve, so she writes all of her desires in a journal. Putting pen to paper works for her. Suddenly, two handsome men (played by Colin Firth and Hugh Grant) set their sights on winning her affection. This rom-com became so popular, it turned into a franchise with two sequels: Bridget Jones: The Edge of Reason (2004) and Bridget Jones’ Baby (2016).

Guess Who (2005)

If you’ve ever wondered what Bernie Mac would be like as your father-in-law, you must watch Guess Who. When a newly engaged couple (played by Ashton Kutcher and Zoë Saldana) visit her father for the first time, the patriarch is surprised to find out her fiancé is white. Will her tight-knit family fall in love with him or will he be leaving the house a single man?

Just Friends (2005)

Just Friends explores a classic glow-up storyline. Ryan Reynolds plays Chris Brander, an unpopular, braces-wearing high-school kid who’s in love with his best girl friend (Amy Smart). When she “friend zones” him as teenagers, he takes that rejection and turns it into fuel for living his best life later on as a music executive in Hollywood. But when he returns home years later over the holidays, they meet up again. Will she look at him in a different light this time around?

Wedding Crashers (2005)

Two womanizing best friends, played by Vince Vaughn and Owen Wilson, are in the business of crashing weddings to meet women. When they make their way to the wedding of the U.S. Secretary of Treasury’s (played brilliantly by Christopher Walken) daughter, things take a turn. Wilson’s character falls for one of his other daughters — played by Rachel McAdams. Only problem? She’s already got a hyper preppy fiancé (played by Bradley Cooper). Watch the star-studded cast duke it out in Wedding Crashers.

Along Came Polly (2004)

Reuben Feffer (one of the greatest character names ever played by Ben Stiller) analyzes risk for a living. But he forgets to consider the odds that his wife might cheat on him with a scuba instructor on their St. Bart’s honeymoon. When he tries to get his life in order after their disastrous post-wedding trip, he runs into an old (and very non-committal) classmate Polly Prince (played by Jennifer Aniston). Will his risk analysis of their potential relationship leave him heartbroken once again?

Deliver Us From Eva (2003)

Eva Dandridge, played by Gabrielle Union, always seems to butt into her three sisters’ love lives. But their men have had enough. So they devise a plan to distract her by paying a suave ladies’ man (played by LL Cool J) to wine and dine her. Except…you guessed it…he ends up catching genuine feelings for her. Will the truth behind who he really is come out?

The Proposal (2009)

When a high-strung New York-based publishing executive (played by Sandra Bullock) finds out her visa application to stay in the U.S. is denied, she forces her lowly assistant (played by Ryan Reynolds) to propose to her so she doesn’t have to return to Canada. When they head to his hometown for the wedding, feelings fly. Will she be able to stay in the U.S. after all?

Legally Blonde (2001)

Elle Woods became a household name after the release of Legally Blonde in 2001. The only thing on this uber-feminine sorority gal’s mind is getting engaged to her college sweetheart after graduation. But when she finds out her prince charming isn’t so charming after all (he leaves her for “more of a Jackie, not a Marilyn”), she works hard to get accepted into Harvard Law School (where he’s heading) to win him back. Along the way, she realizes he’s not her key to success — she is.

What Happens in Vegas (2008)

We’ve all heard about couples heading to Vegas’ little white chapel for an impromptu wedding. But you don’t usually hear about two strangers blacking out, getting married, and then winning a $3,000,000 jackpot on a slot machine after realizing they’re very incompatible. That’s the scenario of this wild rom-com featuring Ashton Kutcher and Cameron Diaz, who must try to make their “marriage” last so they can split the winnings.

13 Going on 30 (2004)

All 13-year-old Jenna Rink wants is to finally be 30 (and have boobs). She gets her birthday wish and wakes up 17 years later as her future self — a fashionable New York City magazine editor. As she adjusts to her new life, she tracks down her old BFF and realizes some years aren’t worth skipping.

The Sweetest Thing (2002)

Think you can’t find romance in a club? The Sweetest Thing proves that theory wrong. Serial dater Christina Walters, played by Cameron Diaz, vows to give up dating after a series of bad flings. But after reluctantly tagging along for a nightclub night in San Francisco with her two besties (played by Selma Blair and Christina Applegate), she (literally) bumps into the potential man of her dreams.

Two Can Play That Game (2001)

Shante Smith (played by Vivica A. Fox) knows the dating games men play — and she makes sure her boyfriend, Keith Fenton (played by Morris Chestnut), doesn’t partake in any of this frivolity. But when he sets his sights on someone else, she puts together a game plan to win back his full affection. Only problem? Keith’s best friend knows all the games women play and lets his friend in on those secrets. Hence: two can play that game. Will they realize love is anything but a game?

Princess Diaries (2001)

Anne Hathaway plays the iconic Mia Thermopolis in Princess Diaries. Mia is an ordinary San Francisco teen who, one day, finds out her grandmother (played by the enchanting Julie Andrews) is actually the queen of a fictional province — Genovia. So, that makes Mia the “Princess of Genovia.” This endearing coming-of-age tale thrusts the spotlight on the typical teen. But along the way she realizes her no-frills approach to life (and romance) is better than the lifestyle many dream of.

Whatever It Takes (2000)

Whatever It Takes plays on good ol’ teenage romance. Sometimes you have to play hard to get (even if you’re actually in love with the person). At least that’s the advice a high school jock, played by James Franco, gives to an ordinary Joe classmate, played by Shane West. West’s character is obsessed with winning over the most popular girl in school. But will acting as if he doesn’t like her actually turn her on? Or is this a disaster waiting to happen?

What A Girl Wants (2003)

Amanda Bynes plays Daphne Reynolds, an American teen who grows up with her single mom in New York City. Her one goal in life? To meet her dad. Except he’s the Prime Minister of the U.K. and he doesn’t know she exists. When she books a one-way flight to London to meet him, both of their worlds turn upside down. And in the end, her heart gets captured by two men — her father, and also a rebellious young Englander. Fun fact: This movie has an incredible soundtrack featuring the likes of The Clash, Willa Ford, and Duncan Sheik.

My Big Fat Greek Wedding (2002)

Windex cures all. That’s what you’ll learn from Toula Portokalos’ Papou (Greek for grandfather) in My Big Fat Greek Wedding. This hilarious love story explores what it’s like for a non-Greek to enter into a super Greek family through marriage. Nia Vardalos, who both starred in and wrote the film, drew from her personal experience marrying outside the Greek bubble to come up with this hysterical story.

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