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15 Unforgettable Chick Flicks That Defined The 2000s

Consider this your new movie marathon itinerary with your girl
by Ria Esguerra | Jul 24, 2017
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We get it, bro. On most days, we’re all about no chick flick moments too. But see, a TNL (tunay na lalaki) knows how get in touch with his feminine side and let them feels out every now and then. Which is why we’ve rounded up some of the best turn of the 21st century chick flicks for a good old movie marathon session with bae.

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Ready those tissues (for your girl, of course!) and a pen and paper (so you can take down some relationship notes).

Mean Girls (2004)

This one is a classic with iconic lines your girlfriend will be able to recite, from “That’s so fetch!” to Kevin G.’s rap (“Aaall youuu sucka MCs, ain’t got nothin’ on me…”). Yet, she will never get tired of watching it over and over again.

Why you should watch it: You get a peek into girl world (which apparently isn’t quite that different from the animal kingdom) and take a trip down memory lane to peak Lindsay Lohan hotness.

She’s the Man (2006)

This film is actually a rather loose, modern day adaptation of Shakespeare’s play Twelfth Night, with it’s absurd storyline but memorable comedic moments. Who knew tampons make great nosebleed stoppers? Young Channing Tatum, that’s who! Plus, the big football match at the end gets really interesting in more ways than one.

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Why you should watch it: Pre-Twitter meltdown Amanda Bynes 

The Notebook (2004)

It's the romance that pretty much kickstarted the female species’ obsession with Ryan Gosling.

Why you should watch it: You might pick up a few courting tricks from Gosling A.K.A. Noah Calhoun.

How to Lose a Guy in 10 Days (2003)

This film drew on the clichés set by its predecessors and essentially created a story around them. It really highlighted the push-and-pull dynamic between the leads, and Kate Hudson and Matthew McConaughey sold it.

Why you should watch it: Kate Hudson’s character’s exaggerated attempts to get McConaughey’s character to break things off can prepare you for relationship speedbumps you’ll have to endure in the future. 

Wimbledon (2004)

It’s a high stakes tennis love story featuring Kirsten Dunst and pre-Marvel Cinematic Universe Paul Bettany.

Why you should watch it: Seeing Bettany before bulking up to take on the mantle of The Vision will make you say, “If he can do it, so can I!”

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(500) Days of Summer (2009)

C’mon, don’t pretend like you haven’t seen this before! It’s the Annie Hall rip-off that resonated deeply with your hipster heart, made everyone say, “I love The Smiths!” and catapulted Zooey Deschanel's career into a different stratosphere.

Why you should watch it...again: Because everyone will have been able to relate to Tom, at one point or another in their lives.

Coyote Ugly (2000)

It's a #throwback to when dancing on top of bars was a big thing. Fun times!

Why you should watch it: The plot may not be groundbreaking, but it stars former Hollywood darling Piper Perabo in racy dance numbers. Plus, Leann Rimes. Drool.


Bring It On (2000)

Bring It On introduced a ton of new jargon to the world, like “cheer-ocracy” and “spirit fingers." It’s like the Pitch Perfect of the early 2000s, and the cheerleader film that launched a thousand sequels. Okay, maybe just five, but it’s a franchise that still keeps on giving, with the latest installment set to be released next month on DVD.

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Why you should watch it: Kirsten Dunst, Gabrielle Union, and Eliza Dushku (from Buffy the Vampire Slayer, Tru Calling, and Dollhouse) in cheerleader uniforms

Forgetting Sarah Marshall (2008)

This film follows how tall, dorky dude Peter (played by Jason Segel of How I Met Your Mother fame) copes with getting dumped by rising star Sarah Marshall (played by Kristen Bell). Hawaii, Mila Kunis, and Katy Perry’s former-beau Russell Brand are thrown into the mix, and you get a lot of laughs while commiserating with Peter who’s just trying his damned hardest to forget Sarah Marshall.

Why you should watch it: They’re not afraid of showing the ugly, messy, and pathetic side of breakups. Although in the end, you can’t help but feel that Peter’s still quite the lucky guy...

The Rebound (2009)

As if going through a divorce is not hard enough, Catherine Zeta-Jones has to deal with falling for her 25-year old male nanny who was supposed to just be her rebound.

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Why you should watch it: Catherine Zeta-Jones is like fine wine. Plus, this film lets you in on what it takes to date an older woman.

If Only (2004)

Your girlfriend will probably still remember the lyrics to this film’s OST Love Will Show You Everything the moment she hears it. 

Why you should watch it: It’s a great reminder to value the people around you and let them know how much you care.

Blue Crush (2002)

Kate Bosworth stars as broke but promising young surfer Anne Marie who works as a hotel maid by day to scrape by while training to become a famous sponsored pro on the weekends. Oh, and our fave badass Michelle Rodriguez is in the movie too.

Why you should watch it: Awesome surfer babes rule!

50 First Dates (2004)

Yet another rom-com set in the island of Hawaii, this Drew Barrymore and Adam Sandler flick made The Beach Boys’ Wouldn't It Be Nice a hopeless romantic anthem for the Adam-Drew tandem generation.

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Why you should watch it: You apparently can learn a thing or two about love from the Sandman. 

The Lake House (2006)

A time-warping mailbox allows Keanu Reeves and Sandra Bullock to exchange letters and communicate instantaneously even while they’re living two years apart. It’s all a bit confusing really, but the characters’ struggles will have you shedding man-tears.

Why you should watch it: The late great movie critic Roger Ebert gave it a 3.5 out of 4 stars. Take his advice: Let go of the logical flaws and inconsistencies of the premise and allow yourself to just feel the emotions, why don’t you?

The Sweetest Thing (2002)

An early aughts chick flick list without a single Cameron Diaz film? Blasphemy! Some of the most iconic scenes from this movie include a blow job gone wrong (you’ll probably never see Aerosmith’s I Don’t Want to Miss a Thing the same way again), a glimpse of ladies room action when women all go together, and a far from boring road trip sequence.

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Why you should watch it: Cameron Diaz, bro. The. Cameron. Diaz


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