A Cynic’s Guide to Valentines Films

With February well and truly in full- swing, a certain themed holiday looms on the horizon. Sparking joy in some and a sense of bleakness in others, Valentine’s Day has become a hallmark for hopeless romantics and cynics alike. And depending on which side of the spectrum you fall—whether your ideal Valentine’s weekend involves marathoning a plethora of classic rom-coms with your partner, or if you’re something of a Joel Barish a la Eternal Sunshine of the Spotless Mind and are more predisposed to the notion that “Valentine’s Day is a holiday invented by greeting card companies to make people feel like crap”—your choice of cinema over the next few days may look a little... different.

But worry not—the lovebirds can spend this weekend Letterboxing When Harry Met Sally... and What If? til the cows come home. Here at The Saint, we’ve got you sorted with an array of films to warm even the coldest of cynical hearts this Valentine’s Day.

Legally Blonde (2001) Let’s kick things off with the original girlboss, the bitch doing the most, the character who served when no one else could: Elle “What, like it’s hard?” Woods. 2001’s Legally Blonde was, and I don’t say this lightly, a cultural reset. It was certainly a refreshing take to have an ostensibly ditzy blonde character be academically empowered, as opposed to vilified and barely competent. Elle’s hard work and drive (and perhaps a little bit of pettiness, let’s be real) are what got her into Harvard Law School. Her work ethic undoubtedly influenced a lot of young viewers— myself included—to push themselves academically. And hey, if love’s not on the cards, maybe getting a 20 on your next assignment is.


Legally Blonde wraps up in a heartwarming way (spoilers ahead!)— Elle befriends Vivian, a previous foe with whom she competed for the affection of her ex-boyfriend Warner, epitomising the “bros before hoes” rhetoric I’m sure so many of us are adopting this Valentine’s Day. It’s a wonderful tale of the importance of female solidarity and friendship above shitty exes, and Elle—now Valedictorian of her Harvard graduating class—leaves Warner behind in a blaze of glory. If you’re all about moving on from exes, focusing on your friendships and excelling in academia, Legally Blonde is a hilarious must-(re)watch this Valentine’s Day.

Marriage Story (2019) You’ll either love it or you’ll hate it, but 2019’s Marriage Story is undoubtedly a staple of modern romantic drama done impeccably. Drawing on his real life experience of a recent divorce, writer and director Noah Baumbach executes the separation of Nicole (Scarlett Johansson) and Charlie (Adam Driver) with aching perfection. Maybe not one to watch if you’ve just recently ended things with someone, but definitely recommended viewing if the dust has settled and you’re now eager to watch someone else’s relationship fall apart. Schadenfreude and all that.

The infamous explosive fight scene between Driver and Johansson (“Every day I wake up!”) is certainly a highlight of the film, but it’s the nuances in the less dramatic scenes that make this movie a standout. It really readjusted my perspective of relationships—sometimes loving someone isn’t enough to keep things alive—and made me realise how, when the honeymoon period draws to a close, the relationship takes a lot of active work to sustain. And even then, oftentimes it doesn’t work out. It’s a pretty sad movie for a seemingly mundane plot, but one that’s definitely worth checking out this Valentine’s Day if you missed its 2019 hype.

Gone Girl (2014)

The ultimate “good for her” film, 2014’s Gone Girl—directed by the ever-captivating David Fincher—delivers one of the best anti-romance movies of the modern era. I’ll try not to lean too heavily into spoilers, but Amy’s (Rosamund Pike) “cool girl” monologue as she leaves her life behind is nothing short of incredible, and the movie deserves at least one Academy Award for its inclusion alone. If you take nothing else from this article, check out the monologue on YouTube. Life-changing.


Anne Hathaway famously joked that Gone Girl is her favourite romantic comedy—and she’s not entirely all that wrong. The film manages to pepper in a healthy dose of dry humour alongside the deterioration of Amy and Nick’s (Ben Affleck) relationship, and it makes the plot that bit more captivating and engaging. The casting is excellent, and you can’t help but root for Amy as she gets her sweet, sweet revenge against Nick and lives out her convoluted masterplan. Amy is perhaps the perfect anti-hero, and Rosamund Pike’s performance is nothing short of stellar. If you haven’t yet had the pleasure of checking out Gone Girl, it’s essential viewing this Valentine’s Day for all the cynics out there. Akin to Legally Blonde, it’s girlbossery to the nth degree and will have you thanking your lucky stars you never got married to Ben fucking Affleck.

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