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Our Favorite Romantic Comedies

odds & ends


5 min read

Thinx - Periodical - Our Favorite Romantic Comedies

by Team Thinx | 02/14/2019

Happy Valentine’s Day from Team THINX, y’all!

Around here, we’re a little more into Galentine’s Day (and discounted chocolate on February 15, of course), but I’m just gonna say it: Who isn’t a sucker for a good, old-fashioned—emphasis on old-fashioned, tbh—romantic comedy?

It’s 2019 — we can roll with some traditional gender roles, *without* taking off our critical feminist hats. 💇

I asked a few people at THINX HQ what they’re queueing up tonight, and here’s what they had to share:

While You Were Sleeping (1994)

Kelsey, Brand Copywriter

What is not to love? There is Christmastime in Chicago, Peter Gallagher's eyebrows, Bill Pullman looking positively dreamy in denim jackets and flannel, and an American icon, Sandra Bullock! It's the kind of love story that you crave when seeking comfort or coziness.

Romantic comedy legend, Sandra Bullock, plays Lucy Moderatz, a lonely CTA worker in Chicago who dreams of falling in love and having a family, as both of her parents have passed and she doesn’t have one of her own. Lucy dreams of Peter in particular, a handsome, successful-looking man who’s always kind to her when she issues him his train token (this is 1995, friends).

On Christmas Day, Peter is pushed onto the tracks in a robbery and Lucy heroically jumps onto the tracks to save him. When he’s unconscious in the hospital, some miscommunication leads to Peter’s entire family thinking Lucy is Peter’s fiancee, and she’s not sure how to tell them the truth. Only Peter’s charming, furniture-making brother, Jack, suspects something is up, and 2 hours of hilarity, hijinks, and sniffling ensue (warning: the end is a tearjerker/will make you believe in true love).  Lucy is looking for someone not just to love, but to be her family and travel the world with her.

The movie is clever and cheeky and warm, and gives you the ending you so desperately want. It reminds you that life doesn’t always go as planned, and if you’re lucky, it will be even better than you imagined. Wow, my cold heart has completed defrosted. Thank you, Sandy!

10 Things I Hate About You (1999)

Sam, EveryBody Program Associate

For me, a registered sucker for quippy dialogue and the melding of Serious Literature™ (trivia: 10 Things I Hate About You is a *liberal* adaptation of The Taming of the Shrew) with mainstream teen entertainment, 10 Things I Hate About You checks a lot of boxes.

Unrealistically well-worded feminist tirades from Kat? Check. The English teacher, Mr. Morgan, hilariously shutting down his students’ bullshit while delivering astute racial commentary? Gold. Everything Allison Janney’s erotica-writing guidance counselor character says? Perfection.

However, it doesn’t escape unscathed from the questionable social messaging of many ‘90s teen movies. Some key aspects that do not hold up: every character of color is completely free of depth or narrative arc,  the term “crack whore” is a casual punchline, and a girl who’s falling-over drunk is literally passed to a dude to make out with.


So, yes, a degree of switching off of my liberal-arts killjoy brain is required for full enjoyment of this film, but once that switch is flipped, this movie is like a warm bubble bath made of Shakespeare-infused teen banter, Heath Ledger’s grin (which truly had me, my girlfriend, and our lesbian relationship weak at the knees for hours), and the fiery joy of butterfly-appliqué baby tees.

13 Going on 30 (2004)

Rachel, Brand Copywriter

Like Jenna Rink, I really, really wanted to be a well-adjusted adult in the *real world*—you know, “30, flirty, & thriving”—when I was a kid. (Tbh, I’m still kind of waiting to magically wake up one day as a super successful editor with a walk-in closet.)

13 Going on 30 is an incredibly cheesy movie, but Jennifer Garner as a 13-year-old trapped in a 30-year-old’s body is charming enough to make its corniest moments—like the intensely choreographed “Thriller” dance scene and the “Love is a Battlefield” karaoke party—fun as hell. Plus, it has everything I want in a rom-com: a relationship that you actually find yourself rooting for (with an adorable Mark Ruffalo!), Judy Greer as a BFF, and a killer soundtrack that mixes ‘80s/early-2000s hits. It's a gem.

When Harry Met Sally (1989)

Brianna, Content Editor

Aside from Valentine’s Day itself, I’m not sure there’s anything more heteronormative and (intentionally? thoughtfully?) problematic and sexist than the plot of When Harry Met Sally. It literally pivots around the question “Can men and women really be friends?” The answer to which I couldn’t care less about.

But witnessing Meg Ryan’s early interpretations of the manic pixie dream girl persona *and* Billy Crystal’s brief and confusing foray into being a ‘90s sex symbol (extra confusing if, like me, you mostly knew him as Mike Wazowski in Monsters Inc.) is a rite of passage. And, yes, the fake orgasm scene in Katz’s Deli is iconic, but Nora Ephron’s writing is the actual gem of the movie, y’all.

If you can shelf (or laugh at) the sexism, you’ll have a pretty tender viewing experience. Also, after 30 years, it still has a 90% rating on Rotten Tomatoes. That is all.

She’s All That (1999)

Laura, Director of Giveback

Despite its totally flawed premise and problematic gender politics, She's All That will always have a place in my heart (and, sadly, so will Paul Walker and his li’l frosted tips... *holds back tears*).

I remember watching it the first time when I was in middle school and being absolutely gobsmacked about this fantasy California high school universe: Did every graduating class need to learn the same choreographed dance for when their favorite song would blast through speakers? Does everyone get handed keys to a doorless Jeep when they turn 16? Does taking off your glasses and cleaning paint off your overalls really make *that* much of a difference in your attractiveness to jerky misogynists? And why would school leaders let a student show up to what looks like a fairly formal graduation with just a beach ball covering his dick?

This movie is absolutely bonkers (exhibit A: Zack's monologue about "not dropping the ball"), but so ridiculous that I just can't resist tuning in when it's on TV.


BRB, downloading Dirty Dancing as I type. What’s your fave romantic comedy? Share with us in the comments!

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