Rom-coms serve two purposes: to help us envision how much more fulfilling our love lives could be, and to reassure us that at least they’re not this chaotic. The films on this list get even more volatile than usual, as the leads navigate situationships that range from mildly concerning to downright intervention triggering. He runs a secret pick-up business. She has been stalking your hook-ups through the window. He kidnaps you. She psychologically tortures you for a promotion at work. But what unites these flicks is the sadistic pleasure we get from watching them, as well as the occasional erotic thrill. So, if you’re looking for an emotionally and sexually confusing romp as we head into Valentine’s Day weekend, we’ve got you covered.
Sabrina (1954)
Let’s clarify first and foremost that the version of Sabrina we’re discussing here is Audrey Hepburn’s incandescent 1950s iteration, not the lesser remake Harrison Ford signed onto in the ’90s. In the former, Hepburn is a young chauffeur’s daughter looking longingly over the fence at the son of her father’s employer, a rich playboy played by William Holden. He doesn’t notice her in the slightest until she returns years later as a radiant woman (dressed exquisitely, as Hepburn always was, by her IRL friend Hubert de Givenchy). The pair begin a dalliance, which upsets his older brother (Humphrey Bogart) who plans to marry the younger off to a wealthy heiress and thereby secure a business deal. Bogart butts in, and attempts to capture Hepburn’s attention long enough to ink his contract.
Where to Watch: MGM+, Pluto TV, YouTube
The Princess Bride (1987)
Is it wrong to fall for the man who kidnaps you on the night of your forced marriage? Buttercup, heroine of The Princess Bride, would certainly dispute any condemnations. Indeed, she is quite taken with the masked Dread Pirate Roberts, who has been terrorizing her homeland and who she believes murdered her childhood lover in cold blood. On the other hand, the Dread Pirate has a biting wit and is handy with his sword, so who’s to judge? The pair set out on a caper across swamplands and villages as they flee Buttercup’s betrothed who, somehow, is an even less advantageous match.
Where to Watch: Disney+, Hulu
Pretty Woman (1990)
He’s an underhanded businessman. She sells sex. They meet on a street corner, but before long, he’s putting her in designer duds and taking her to a polo game. In the first of Richard Gere and Julia Roberts’s two rom-coms together, the pair overcome their avoidant attachment styles at the intersection of their high-low lifestyles. Of course, he’s paying her for her time, and she’s occasionally more interested in watching I Love Lucy reruns than going down on him, but all’s well that ends well for this unlikely duo.
Where to Watch: Disney+, Hulu
10 Things I Hate About You (1999)
Like many ’90s teen flicks, 10 Things I Hate About You is a modernized Shakespeare adaptation—here reinterpreting The Taming of the Shrew. Instead of ladies and noblemen, a high school bad boy, Patrick (Heath Ledger), is set upon his headstrong classmate, Kat (Julia Stiles). A few conniving underclassmen put him up to it after learning that Kat’s father has instituted a rule, only allowing her younger sister to date after Kat does so herself. The clever man expects his frigid elder daughter likely never will. Enter a young Ledger, who tries every trick up his sleeve to convince her and looks good doing so. There’s drunken dancing on tables, Sylvia Plath references, public serenades, and oh-so-familiar teen angst.
Where to Watch: Hulu
Punch-Drunk Love (2002)
Barry Egan, played by a young Adam Sandler in his first serious role, runs a tchotchke company in Los Angeles and struggles to assert himself to a gaggle of sisters who alternately torment and belittle him. He strikes up a romance with one of their coworkers, which is complicated by his social anxiety, violent outbursts, and tumultuous relationship with a phone sex operator. Throw in altercations with Phillip Seymour Hoffman, pudding sweepstakes, and a mystical harmonium, and you’ve got yourself a Paul Thomas Anderson film.
Where to Watch: Amazon Prime
Secretary (2002)
James Spader and Maggie Gyllenhaal play attorney and secretary in this erotic romp. After leaving a mental institution, where she was placed following a self-harm incident, Gyllenhaal’s character takes up the new position, and quickly learns of her boss’s more eccentric proclivities. Before long, he’s spanking her over his desk and having her seductively retype memos ad nauseam, much to her delight. Their romance is unconventional, and certainly a workplace violation, which spooks our protagonists as much as it pushes them toward each other.
Where to Watch: Rent on Amazon Prime
How to Lose a Guy in 10 Days (2003)
She’s a fast-talking magazine writer who pitches her editor a story on how to get a guy to dump you within 10 days. He’s a faster-talking ad exec who bets his boss he can get any woman to fall in love with him to win an account. Leads Matthew McConaughey and Kate Hudson spend the next 116 minutes torturing each other through increasingly incredulous means (think, sobbing at your boyfriend’s poker night), as they both try to win their covert and contradictory wagers. But when the chemistry is this good, a relationship founded entirely on sadistic lies becomes more irresistible with every minute that ticks by.
Where to Watch: Peacock, Paramount+
Down with Love (2003)
It’s an intentionally camp “no-sex sex comedy” slandered by critics, featuring two celebrities who treat it as nothing more than a hazy blip on their IMDb. The barely profitable early aughts romp is a diamond in the streaming rough that sees Renée Zellweger write a bestselling self-help book urging women to adopt a no-strings sex lifestyle. As a foil, a lowkey meninist played by Ewan McGregor schemes to make her fall in love with him so he can expose the flaws in her worldview. But that’s not even the red flag that earned this film a spot on the list. There are enough twists and turns in Down With Love to make even the most avid rom-com expert dizzy.
Where to Watch: Rent on Amazon Prime or Apple TV
Hitch (2005)
In New York, Alex “Hitch” Hitchens (Will Smith) makes a living by coaching insecure men on how to secure romantic relationships with women. There are dancing lessons, pep-talks, and flirty conversation pointers. His clients include a variety of mopes played by mid-aughts comedy staples like Kevin James. But then, Hitchens meets the whip-smart Sara Melas (Eva Mendes), and all of a sudden, he finds himself hiding his lucrative practice from her scrutinizing gaze. What’s more, none of his usual schemes are turning her head.
Where to Watch: Rent on Amazon Prime or Apple TV
Lars and the Real Girl (2007)
In a small town, Lars Lindstrom (Ryan Gosling) lives a secluded life in the garage behind his brother and sister-in-law’s home. The latter does her best to draw Lars out to socialize until, finally, one night, he announces that he and a guest will join them for dinner. When the pair arrive at the main house, Lars’s guest reveals herself to be a sex doll he bought online. He treats Bianca, as he’s named her, as if she were a real person and, sympathetic to his struggles, the inhabitants of his small town begin to play along.
Where to Watch: Amazon Prime
Silver Linings Playbook (2012)
Following eight months spent in a mental health facility treating his bipolar disorder, Bradley Cooper’s character returns home with a new lease on life, as well as a slapdash plan to win back his ex-wife. A friend of a friend, played by Jennifer Lawrence, offers to help him out in exchange for his participation in an upcoming dance competition. Lawrence’s character, battling her own we-know-not-what, toys and flirts with Cooper across 122 increasingly stressful minutes that toggle between helpful and outright detrimental to their respective recoveries.
Where to Watch: Rent on Amazon Prime
The Big Sick (2017)
Before Kumail Nanjiani was a swole Marvel man, he was well-known for writing and starring in this offbeat rom-com about a Pakistani man and his white, comatose ex-girlfriend. Nanjiani plays a somewhat successful stand up being pressured to give up his day job and marry within the culture by his parents. Zoe Kazan plays his love interest, who dumps him before falling into a coma and forgetting to tell anyone she’s newly single. Of course, when Nanjiani appears at her bedside, misunderstandings ensue.
Where to Watch: Amazon Prime
The Half of It (2020)
Gosh, high school is messy. In this love triangle (square?), popular girl Aster is dating popular boy Trig. But, unpopular girl Ellie and unpopular boy Paul are both secretly in love with her. Paul convinces Ellie, who regularly earns extra cash by ghostwriting essays for her classmates, to write love letters on his behalf. She goes along with the deception, despite having fallen for the same girl, because she’s been using the money to help support her family. What follows is a series of crossed wires, love confessions, crushes on lesbians (ouch), and some good old-fashioned coming-of-age angst. We’ve all been there—sort of.
Where to Watch: Netflix
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