The best romantic comedies to watch on Hulu

Is it too early to celebrate Valentine's Day? Hulu's selection of rom-com films, from Say Anything to Fire Island, suggests no

By The A.V. Club | January 14, 2023 | 2:00pm

Film Features Hulu

The best romantic comedies to watch on Hulu

(Clockwise from bottom left:) Rosaline (Courtesy of 20th Century Studios), Fire Island (Courtesy Searchlight Pictures), Friends With Kids (screenshot), Palm Springs (Hulu) Graphic: The A.V. Club

Is it too early to celebrate Valentine’s Day? Trick question: any night can be a date night. And if you want that date to involve curling up with a romantic comedy, the streaming library over on Hulu has you covered. From cinematic classics like Say Anything to recent hit originals like Palm Springs and Fire Island (and their latest, January 13’s The Drop), Hulu’s rom-com offerings are as strong as any of its other genre categories. For the streamer’s top titles overall films, click here. But for the best available films that combine comedy and romance, and The A.V. Club’s writing on each, read on for our expert recommendations.

This list was updated on January 13, 2023.

Enough Said

ENOUGH SAID: Official HD Trailer

[Nicole] Holofcener specializes in intermittently amusing big-screen sitcoms about the follies and foibles of privileged, city-dwelling women. Obstacles facing her characters have included protecting the family inheritance from a spendthrift husband, waiting on an elderly neighbor to croak in order to expand into her adjacent apartment space, and finding the right time and way to fire the incompetent maid. That last example comes from Holofcener’s latest comedy, Enough Said, but it’s by far the most groan-inducing element of the film. On the whole, this is one of the writer-director’s stronger efforts, largely because it bursts out of the class bubble in which so many of her movies take place and into more universally relatable territory. Yes, the characters are still white financially stable urbanites. This time, though, their problems are not specific to their tax bracket.Displaying little of the testiness typical of her Elaine Benes or Vice President Selina Meyer characters, Julia Louis-Dreyfus is charming as a divorced mother and middle-aged masseuse, prepping for the departure of her college-bound daughter (Tracey Fairaway) and growing increasingly unhopeful about her romantic prospects. At a party, she meets a poet (Catherine Keener), who becomes a friend and client, and a fellow single parent (James Gandolfini, in his penultimate role), with whom she becomes hesitantly and then rapturously involved… []

Fire Island

FIRE ISLAND | “Heads Up” Clip | Searchlight Pictures

It doesn’t take long for , Joel Kim Booster’s instant-classic Jane Austen riff, to stake its claim in the romantic comedy canon—or rather, defiantly outside of it. Less than a minute into the opening sequence, Booster refers to Pride And Prejudice, his source material, as “hetero nonsense.” As this story’s Lizzie Bennet stand-in, gay Brooklynite Noah continues to narrate: he shudders at the “boyfriend energy” of the naked man in his bed whose name clearly eludes him, then calls his chosen family, the group of friends on their annual Fire Island vacation, the F-word (the one reserved for gays). “Don’t cancel me,” he tells us, tongue firmly in cheek. “I’m reclaiming it!”Suffice it to say this isn’t your typical rom-com—but then again, how could it be? With all due respect to and rather less respect to Love, Simon, queer audiences haven’t seen themselves reflected much in a genre that, at least in its heyday, defined Hollywood’s mainstream and reinforced heteronormative sociocultural standards. Booster and director Andrew Ahn use Austen’s tale of class tension, a romantic comedy urtext, to laugh in the face of such standards, and introduce some new ones. Queer and straight viewers alike may experience with a mix of delight and disorientation; they haven’t worked the muscles of watching a gay will-they-won’t-they story, let alone one populated by unabashedly out characters. [Jack Smart]

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The 40-Year-Old Virgin

The 40 Year Old Virgin (1/8) Movie CLIP - Are You a Virgin? (2005) HD

The generally winning, big-hearted Steve Carell vehicle The 40-Year-Old Virgin is funny and realistically romantic, but almost never at the same time… Making a surprisingly graceful transition to a leading-man role, Carell stars as a middle-aged L.A. electronics-store employee whose action figure-filled apartment helps explain why he’s managed to put off sex for so long. At least one of his buddies/co-workers suspects that behind his creepily nice façade lurks a serial killer, but after news of Carell’s sexual inexperience slips out, his co-workers set about helping him lose his virginity. Meanwhile, Carell begins an intentionally platonic romance with [Catherine] Keener that sets him stumbling onto the path of emotional maturity. [Nathan Rabin]

Friends With Kids

While it’s true that most romantic comedies merely make minor tweaks to a rusted-out formula, it’s also true that many critics approach rom-coms with a sense of eye-rolling obligation, while solidly unspectacular movies like Lockout get praised to the skies. There’s formula in Jennifer Westfeldt’s directorial debut, but feeling as well. And anyone who thinks it’s far-fetched to see two friends of opposite gender agreeing to raise a child while they continue to date other people hasn’t touched base with single urbanites in their late 30s recently. (It’s absurd, but only by about 10 percent.) If nothing else, the film deserves endless praise for its bombshell kicker, a final line that blasts through the coy innuendo at the heart of most screen romances. []

Happiest Season

Mix with , add a touch of , and give the whole thing a lesbian makeover, and you’ve got Happiest Season, Hulu’s holiday rom-com starring Kristen Stewart and Mackenzie Davis. If that makes the film sound a touch derivative, that’s kind of the point. Writer/director/longtime lesbian icon Clea DuVall set out to put a queer spin on the sort of comforting, feel-good holiday romances that straight audiences have been enjoying for decades. And like the similarly trailblazing teen movie , that means Happiest Season feels like nothing you’ve seen before and also like a lot of things you’ve seen before. []

Love, Simon

Love, Simon | Official Trailer 2 [HD] | 20th Century FOX

Love, Simon opens with narration from its teenage protagonist Simon Spier (Nick Robinson) explaining, with what seems like maximum presumption, that he’s “just like you.” He proceeds to describe a thoroughly upper-middle-class existence that includes a spacious, well-appointed home; high-achieving yet ever-present and caring parents (Jennifer Garner and Josh Duhamel); an overly art-directed bedroom decorated with perfect self-expression; money and a car for daily iced-coffee runs; and a close cadre of well-scrubbed yet diverse friends who carefully and conveniently self-censor their language to stay comfortably within the confines of a PG-13 rating. He’s just like you, assuming you live in a teen soap or possibly a car commercial… it’s revealed a little later that Simon is not actually talking to the audience, swapping a rhetorical “you” for a specific one. The explanation of his picture-perfect life, and also the secret he’s carrying with him, is addressed to an anonymous internet pen pal he calls Blue. Simon finds Blue’s email address on a PostSecret-like website where students at his high school upload confessions, and they bond over their common ground: They’re both closeted gay kids. []

Palm Springs

Andy Samberg stars as Nyles, a slacker doofus stuck at a destination wedding in Southern California, which he’s attending as the date of a bridesmaid. Blithely wandering the reception in a loud and very informal short-sleeve shirt, Nyles clearly doesn’t have any fucks to give. But he also seems to have a suspiciously premonitory sense of how the night will play out. And before long, Palm Springs reveals the reason for both: He’s stuck in a time warp, waking up every morning to find himself still in Palm Springs on the morning of the wedding. The film employs its magical conceit as a multi-purpose metaphor for a long-term relationship. The flip side, of course, is that monogamy can leave you feeling as stuck as the characters, living the same day over and over again, with only your significant other for company. But Palm Springs wears all that baggage lightly. It’s a sadly rare thing: a sweet, madly inventive, totally mainstream romantic comedy, buoyed by inspired jolts of comic violence (some of them provided by J.K. Simmons as another wedding guest with a very big bone to pick with Nyles). []

Rosaline

If the name Rosaline rings a bell, it’s because she’s the mentioned-but-never-seen girlfriend Romeo was dating right before falling for his one true love in William Shakespeare’s Romeo And Juliet. Yet in director Karen Maine’s feature , the character once regarded as a footnote becomes the lead, guiding a hilariously irreverent and empowering re-fashioning of that tale of woe. Crafting a comedy from the perspective of the Bard’s minor characters isn’t exactly new, as Tom Stoppard’s Rosencrantz And Guildenstern Are Dead did the same with Hamlet, but the innovative idea is reinvigorated with witty dialogue, a solid ensemble and astute direction. []