Every Valentine’s Day, the same titles trend. The Julia Roberts megahits. The Kate Hudson comfort rewatches. The Reese Witherspoon charm offensives. The Sandra Bullock slow-burns. And, if you’re feeling windswept and literary, perhaps another brooding dive into “Wuthering Heights” and its stormy declarations of doomed love.
But what if this year you skipped the obvious?
If you’re in the mood for romance with a little edge, wit, chaos or political bite – something you may not have already memorised line for line – here are five underrated romantic comedies worth seeking out this Lover’s Day.
Long Shot (2019)
On paper, a Seth Rogen/Charlize Theron political rom-com sounds like a novelty. In execution, Long Shot is far sharper – and sweeter – than it has any right to be.
Theron plays Charlotte Field, the impossibly polished U.S. Secretary of State positioning herself for a presidential run. Rogen is Fred Flarsky, an unemployed, proudly scruffy journalist who once had a teenage crush on her – and who suddenly finds himself hired as her speechwriter.
Yes, there’s outrageous humour (including one extremely viral scandal that derails a campaign), but beneath the R-rated gags is a genuinely thoughtful exploration of image, gender politics, and the impossible standards women in power face. Theron is dazzlingly controlled; Rogen brings surprising vulnerability. Together, they create an odd-couple chemistry that feels both absurd and oddly grounded.
It’s a big studio rom-com that actually has something to say – and still delivers the swoon.
Available to stream on HBO Max.
I Could Never Be Your Woman (2007)
Written and directed by Amy Heckerling (Clueless), this Michelle Pfeiffer/Paul Rudd romance quietly slipped through the cracks – and never quite received the love it deserved.
Pfeiffer plays Rosie, a 40-something TV producer navigating industry ageism, single motherhood, and her own internalised anxieties about growing older. Enter Rudd’s charming 29-year-old actor, who falls for her without hesitation – even if she can’t quite believe it herself.
What makes this one special is its honesty about aging, insecurity and self-sabotage. Pfeiffer is luminous and deeply human, and Rudd radiates warmth rather than irony. There’s also a whimsical thread involving an imagined Mother Nature figure that gives the film a surprisingly reflective tone.
It’s not flashy. It’s not glossy. But it’s tender, funny and emotionally resonant – and wildly underrated.
Available to stream on Prime Video.
Down with Love (2003)
Some films are simply ahead of their time.
When Down with Love landed in 2003, audiences didn’t quite know what to do with its hyper-stylised homage to 1960s “no-sex sex comedies.” But two decades later, Peyton Reed’s technicolour confection feels downright ingenious.
Renée Zellweger plays a feminist author preaching independence from men. Ewan McGregor is the smug magazine writer determined to make her fall in love as part of an elaborate ruse. What unfolds is a meticulously crafted pastiche of Doris Day/Rock Hudson bedroom comedies – complete with split screens, innuendo and rapid-fire dialogue – that ultimately flips the genre on its head.
It’s clever. It’s camp. It’s aesthetically immaculate. And its final act twist is far more subversive than many rom-coms that came after it.
Available to stream on Prime Video and Disney+.
The Sweetest Thing (2002)
Dismissed at the time as just another raunchy early-2000s girls’ night-out movie, The Sweetest Thing deserves reconsideration.
Yes, it’s outrageous. Yes, it’s crude. Yes, there are exploding toilets and wildly inappropriate public mishaps. But at its heart is a surprisingly sincere romantic structure – and, more importantly, a celebration of female friendship.
Cameron Diaz’s Christina is a self-proclaimed commitment-phobe who suddenly finds herself shaken by an unexpected connection. The road-trip chaos that follows is pure early-aughts energy, but the film’s real strength lies in the dynamic between Diaz, Christina Applegate and Selma Blair.
It’s messy, fearless and unapologetically female – and its cult status feels increasingly justified.
Available to purchase on Prime Video and Apple TV.
Going the Distance (2010)
Before long-distance relationships became a FaceTime norm, Going the Distance tackled modern romance with refreshing frankness.
Drew Barrymore and Justin Long play a couple who fall hard during a New York summer – only to face bi-coastal reality when she returns to San Francisco. What follows isn’t just grand gestures and airport chases; it’s awkward phone sex, career compromises, jealousy and difficult conversations about ambition.
Directed by Nanette Burstein, the film feels more grounded than many of its glossy peers. It allows its characters to be flawed and occasionally selfish – and ultimately suggests that timing and geography matter just as much as chemistry.
It’s funny, contemporary and a little more emotionally honest than most romantic comedies dared to be in 2010.
Available to stream on Stan.
Valentine’s Day doesn’t have to mean revisiting the usual comfort classics. Sometimes the most rewarding romances are the ones that slipped past you the first time. So this February 14, skip the predictable. Try something a little unexpected. You might just fall in love with a rom-com you didn’t see coming.
