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Coupled or not, it’s officially rom-com season! We’re giving you our takes on three staples of the genre.

To narrow the playing field, this list is focused on flicks that graced our screens in the early aughts. Three staff members, Mackenzie Manley, Stephanie Daugherty and Bella Hemsath, will give their takes on each movie. Take a seat, grab some ice cream and get comfy. 

The Princess Diaries (2001)

MM: The sequel definitely leans heavier on the rom-com vibes, but The Princess Diaries is iconic—Fat Louie, the M&Ms pizza, the princess lessons, Julie Andrews starring opposite Anne Hathaway. As a woman with curly hair, glasses, thick eyebrows and public speaking anxiety, the makeover scenes felt targeted, but I love it nonetheless. I was even pre-makeover Mia Thermopolis for Halloween!

BH: Although I’ve probably seen the sequel a million times more than the first (it does feature Hollywood’s best Chris), there is something so classic about the original The Princess Diaries. A classic rags-to-riches story of a girl just like every other, except surprise, she’s a princess! It’s fun, it’s campy, there are sweet relationships between all of the characters, and it is genuinely so heartfelt to watch Mia and her grandmother bond in a messy situation over someone who is no longer with them. It also helps that this movie is endlessly quotable, though it doesn’t feature the iconic mattress surfing scene. C’est la vie, not every movie can be perfect!

SD: I definitely sympathize with being a “Mia pre-makeover” gal, but I feel so seen by Julie Andrews’ facial expressions and Mia’s stress levels while driving that it almost makes up for it! This lighthearted movie is perfect for a casual girls night or to have on in the background while you’re crafting or working on a puzzle.

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Legally Blonde (2001)

MM: While considered a rom-com, Legally Blonde focuses more on Elle’s journey to becoming a lawyer and getting past her loser ex-boyfriend. Embracing pink and hyper-femininity—from Barbie to coquette fashion—is en vogue, but when Legally Blonde was released most blonde, femme characters were either villainized or sidelined as “bimbos.” While the feminist themes aren’t very intersectional, I’ve always admired how this film both flipped the “dumb blonde” trope on its head and embraced it. Pick this for a Galentine’s movie night. Oh, and I’d be remiss not to shout out the iconic Jennifer Coolidge! Legally Blonde is also endlessly quotable. “What, like it’s hard?”

BH: Legally Blonde is both rom-com and courtroom procedural, a hyper-feminine Law and Order, if you will. It features an absolutely bananas court case, intermixed with Elle pining after her “very serious” ex-boyfriend Warren and coming into her own as a law student. Elle may seem ditzy, but she’s hardworking, passionate, has a better LSAT score than Sam Winchester and Rachel Zane. 

SD: Bella, now you’ve got me imagining a cross-fandom law practice run by Elle and Sam (someone start writing the fanfic). I think what I love most about this movie is how Elle stays true to who she is and what she loves, even when everyone else in her environment seems to be the total opposite. Her kindness and work ethic are all wrapped up in pink glitter and it’s absolutely perfect. This movie is one of my go-tos for when I need some motivation to do the hard things so I can have my own “Watch Me Shine” montage alongside Elle!

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The Holiday (2006)

MM: Cameron Diaz, Kate Winslet, Jude Law and Jack Black star in this swoon-worthy holiday rom-com about two forlorn women who swap houses, one in sunny California and the other in snowy England. Listen, I’ve been dreaming about living in the latter’s cozy cottage for years. Is that too much to ask for? 

BH: This movie has everything: young Jude Law, Jack Black as a romantic interest and Kate Winslet as a writer. I watched it with my grandmother and it quickly became one of my comfort rom-coms. The plot of this movie truly lives up to the aesthetics, something that is difficult to do with a cottage that gorgeous. Plus, the different environments of California and England throughout the movie makes this perfect for summer OR winter. 

SD: It is a truth universally acknowledged that a bookish human must have a desire to live in this movie. The cottage. The sweaters. The love interests (hello, single-girl-dad Jude Law!). The nostalgic beauty and wild whimsy of early-Internet days where you could just swap houses with a total stranger on a totally different continent. This movie truly is so cozy and heartwarming, and now I want to curl up on the couch with a mug of tea and my Squishmallow and watch it again haha.

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