21 rom-coms you’ve (maybe) never seen before

Celebrate Valentine's Day with underrated movies from Demi, Eddie, Denzel, Freida, and more

Feb 10, 2025

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Valentine’s Day is a great time to break out the rom-com comfort food, but sometimes it’s nice to mix things up a bit too. And since I spent four years writing twice-monthly essays about romantic comedies for my old A.V. Club column, When Romance Met Comedy, I’ve discovered my fair share of hidden gems.

Last year, I highlighted my 21 favorite rom-coms since 2010. This year, I decided to highlight 21 lesser known rom-coms that also deserve their day in the sun. (And I avoided any crossover between the two lists, so you’ve got double the recommendations.) Now, to be fair, I’ve included some queer classics and beloved Black rom-coms that are definitely part of certain cultural canons. And I’m also banking on the fact that hits for certain generations may be blindspots for others. But hopefully everyone will be able to find at least something they haven’t heard of before on this list.

I also linked to my When Romance Met Comedy articles where applicable, in case you want to read a bit more about these films before or after you watch. Feel free to add your own lesser-known rom-com recs in the comments too!

Bride and Prejudice (2004)

When people debate which Pride and Prejudice adaptation is best, they usually pit the 1995 miniseries against the 2005 film, with a few votes for Bridget Jones’s Diary thrown in. But I’ll also standup for this delightful 2004 version that updates the story into a Bollywood homage set in contemporary India. Written and directed by Bend It Like Beckham’s Gurinder Chadha, Bride and Prejudice is a joyful, sneakily smart update on Jane Austen’s classic, with American/Indian culture clashes subbing in for the class commentary of the novel. And while it admittedly doesn’t have the best Darcy, it does feature Aishwarya Rai as a pitch perfect Lizzy Bennett figure, Naveen Andrews dancing his heart out, and one of the catchiest songs in movie musical history.

About Last Night (1986 & 2014)

Since we’re in the middle of a Demi Moore renaissance, now is the perfect time to check out this sweet, grounded rom-com she made with Rob Lowe back in the mid 1980s. The movie’s big hook is that it doesn’t have a big hook. It just explores what it’s like to enter your first big committed relationship in your twenties. And it got a really solid mid-2010s remake starring Michael Ealy, Joy Bryant, Kevin Hart, and Regina Hall too.

Boomerang (1992)

Between his buddy comedies of the 1980s and his family comedies of the 1990s/2000s, Eddie Murphy made a movie that could have taken his career in a whole new direction—the stylish rom-com, Boomerang. He plays a slick, womanizing advertising executive who gets a taste of his own medicine from his new man-eating boss (Robin Givens). But the heart of the film belongs to his sweet lived-in friendship with pals played by Martin Lawrence, David Alan Grier, and an up-and-coming Halle Berry. Though the mixed reaction to Boomerang seemed to drive Murphy back to his comedic comfort zone, the movie is a welcome glimpse into his less celebrated talents as a romantic leading man.

But I’m A Cheerleader (2000)

Perhaps the biggest cult classic on this list, But I’m A Cheerleader stars a teenage Natasha Lyonne as a high school cheerleader who gets sent off to a gay conversion camp. Ironically, however, it’s not until she arrives in that anti-gay environment that she realizes she actually does like girls—specifically, Clea DuVall’s uber cool lesbian rebel. For a sense of the film’s tone, just know that RuPaul plays one of the program’s proudly ex-gay counselors. And that’s just one of many subversive, surrealist touches. In fact, director Jamie Babbit specially wanted to reclaim camp for queer women—blending John Waters edge with her own earnest love of the rom-com genre.

Down with Love (2003)

Some films are simply too far ahead of the curve to be appreciated in their time. And that’s definitely the case for this Renée Zellweger/Ewan McGregor comedy, which flopped in 2003 but now holds up better than so many rom-coms released in the early aughts. A deeply loving homage to the Doris Day/Rock Hudson “bedroom comedies” of the 1960s, Down with Love follows a womanizing magazine writer (McGregor) who decides to trick a feminist author (Zellweger) into giving up her anti-marriage ways by posing as her dream man. But director Peyton Reed has more than a few tricks up his sleeves when it comes to updating this insanely detailed ’60s rom-com pastiche for the 21st century.

Something New (2006)

Rom-com queen Sanaa Lathan is best known for classics like Love & Basketball and Brown Sugar, but she’s equally great in this lesser known 2006 vehicle about interracial dating. Lathan plays a Type-A career gal who winds up falling for a laidback landscape architect played by Simon Baker. And while the fact that Lathan is Black and Baker is white initially seems like it’s mostly just going to be a light comedic backdrop for their romance, writer Kriss Turner and director Sanaa Hamri eventually bring the topic to the forefront in thoughtful, honest ways.

Shithouse (2020)

Cooper Raiff’s Cha Cha Real Smooth was one of my favorite movies of 2022. But before he made that thoughtful post-grad romance, he made this equally sweet college-set rom-com too. Raiff stars as a lonely college freshman who winds up bonding with his cool-girl RA (Unbreakable Kimmy Schmidt’s Dylan Gelula) when her pet turtle dies. They share a walking-and-talking connection in the vein of Before Sunrise, in a movie that captures all the holdups and anxieties of early college life.

Claudine (1974)

Rom-coms with predominantly Black casts didn’t really become a norm for Hollywood until the 1990s. But Claudine is the welcome exception that proves that rule. It was produced in the mid-1970s by Third World Cinema Corporation, an independent production studio that specifically aimed to tell three-dimensional stories about people of color. And it follows the romance between a single mom played by Diahann Carroll and a garbage man played by James Earl Jones as their love story plays out against the backdrop of a broken welfare system, radical Black activism, and joyful communal defiance.

Mississippi Masala (1991)

When it comes to rom-coms with the hottest stars, Mississippi Masala should certainly be in the conversation. Denzel Washington and Sarita Choudhury steam up the screen in this cross-cultural romance set in Greenwood, Mississippi. And while big screen interracial love stories usually feature a white perspective, director Mira Nair delivers something different here. Denzel plays a carpet cleaner born and raised in Mississippi, while Choudhury is the daughter of a Ugandan Indian motel manager who was forced to leave his African home country in the 1970s. It’s a fraught political background for a high-stakes love story after prejudice, racial hierarchies, and whether the power of love can truly conquer all.

Imagine Me & You (2005)

Before Happiest Season, there was Imagine Me & You—a lesbian love story wrapped up in a classic, cheesy rom-com package. Here it’s Piper Perabo and Lena Headey who swoon over one another against picturesque shots of London and quirky flower shop settings. The twist? They meet cute on Perabo’s wedding day, as she walking down the aisle to marry Matthew Goode. Never fear, however, despite the sky-high martial stakes, this romance takes its cues from Richard Curtis and Nora Ephron and leaves everyone feeling warm and fuzzy by the end, no matter where on the love triangle they fall. Thanks to charismatic work from all three leads (especially Headey), Imagine Me & You proves feel-good rom-com comfort food doesn’t have to be stick straight.

Keeping the Faith (2000)

After bursting onto the scene with intense roles in Primal Fear, American History X, and Fight Club, Edward Norton knew there was only one thing to do next: direct and star in a romantic comedy about a priest and a rabbi who fall in love with the same girl, of course! It’s a hilarious career swerve that also led to a pretty darn charming rom-com. Norton is the priest, Ben Stiller is the rabbi, and Jenna Elfman is the old childhood friend who kicks off a complicated yet empathetic love triangle between them. And while Stiller and Elfman are the main romantic throughline, Norton gets to establish his own Hot Priest cred years before Andrew Scott would do the same.

Love Jones (1997)

After 1974’s Claudine and 1992’s Boomerang both tried and failed to inspire Hollywood to make more rom-coms with Black leads, it was Love Jones that finally got the timing right. In an era where Black cinema was largely focused on urban teen crime stories like Boyz n the Hood, writer/director Theodore Witcher wanted to show a different slice of Black life. Love Jones follows a poet (Larenz Tate) and a photographer (Nia Long) who strike up a passionate but fraught romance in Chicago. It’s a grown-up, bittersweet look at the emotional stakes of a new relationship. And it helped pave the way for a wave of subsequent Black rom-coms like The Wood, How Stella Got Her Groove Back, and The Best Man.

Saving Face (2005)

One of my favorite discoveries from When Romance Met Comedy, Saving Face is one-half lesbian love story, one-half mother/daughter relationship dramedy, and one of the few American rom-coms with an all-Asian cast. Wilhelmina “Wil” Pang (Michelle Krusiec) is a successful surgeon who finds herself falling for a ballet dancer (Lynn Chen). But Wil is too afraid to come out to her conservative Chinese immigrant family, and things get even more complicated when her 48-year-old mom (Joan Chen) shows up on her doorstep pregnant, unwed, and with nowhere else to go. Writer/director Alice Wu combines those storylines into a heartfelt, funny, sometimes fraught, but ultimately joyful celebration of love in all its forms.

The Half of It (2020)

Once you’ve seen Saving Face, you can roll right on through to Alice Wu’s next feature, The Half of It—a Cyrano-inspired high school rom-com 15 years in the making. The Netflix film stars Leah Lewis as an introverted, closeted teen who gets roped into helping a himbo football player (Daniel Diemer) romance their mutual crush (Alexxis Lemire). In the end, however, The Half of It is as much a friendship rom-com as it is a truly romantic one. And that sweet platonic throughline builds to one of my all-time favorite rom-com endings.

Dirty Dancing: Havana Nights (2004)

This forgotten Dirty Dancing spinoff has a pretty unusual origin story. It started as a screenplay by NPR’s Peter Sagal about a real-life American teenager who fell in love with a young Cuban revolutionary during the 1950s. But what was meant to be a serious romantic political drama eventually became… a cheesy Dirty Dancing film! Still, there are fascinating hints of that heavier political throughline here. And you can also enjoy a baby Diego Luna dancing his heart out as the sensitive, charismatic male lead who (literally) sweeps Romola Garai off her feet.

Catch and Release (2007)

This Jennifer Garner rom-com about grief and second chances was a flop at the box office and sits at just a 22% on Rotten Tomatoes. So imagine my surprise when I finally got around to watching it last year and discovered a true hidden gem about a woman healing from the death of her fiancé by surrounding herself with his best friends. As I wrote in my impassioned Letterboxd review, “There is a real epidemic of people assuming that studio rom-coms are trying and failing to be conventional, when actually writer/director Susannah Grant is clearly trying to deliver an off-beat character study about grief within a specific genre framework. And it’s fine not to like the end result, but I worry that people quite literally can’t SEE the end result because their preconceived assumptions about what this genre ‘should’ be leaves them incapable of actually watching the movie that’s in front of them. Also, Timothy Olyphant wears the hell out of some bootcut jeans.”

Just Wright (2010)

Queen Latifah is one of our most luminous rom-com stars—and also one of the first (and still too few) plus-sized women to lead a romantic comedy. And while Just Wright isn’t explicitly about her body type, it is about what it feels like to be the kind of woman who’s perpetually passed over romantically; who’s seen as “the perfect homegirl” and nothing more. Latifah plays a physical therapist who meets cute with an NBA star (Common) only to watch him fall for her bubbly god-sister (Paula Patton) instead. As that love triangle rearranges, however, Just Wright celebrates Latifah as the rom-com Cinderella she is.

Definitely, Maybe (2008)

I’m not always the biggest Ryan Reynold fan, but he’s perfectly deployed as a newly divorced dad in this How I Met Your Mother-meets-High Fidelity look at life and love. When his daughter (Abigail Breslin) demands to know how her parents met, Reynold’s Will decides to change some names and reframe the story as a mystery: Is her mom put-together Emily (Elizabeth Banks), rebellious April (Isla Fisher), or sophisticated Summer (Rachel Weisz)? As Will recounts his 16-year-history with the three women, the movie makes the case that love is a journey, not a destination, and that good things can still come out of a romance that’s not meant to last.

Jeffrey (1995)

Some rom-coms are timeless and others get their power from the way they capture a snapshot of a particular time and place. The latter very much describes Jeffrey, a film about gay male life in New York City during the second half of the AIDS crisis. Steven Weber plays the titular Jeffrey—an anxious aspiring actor who swears off sex only to find himself falling for a hunky HIV-positive bartender (Michael T. Weiss). Based on a play by Paul Rudnick, the film is filled with heightened fantasy sequences and memorable cameos that make it unlike anything else in the rom-com canon. And it also features an all-time great supporting performance from Patrick Stewart.

Mr. Malcolm’s List (2022)

Director Emma Holly Jones’s racially diverse take on a Regency Era romance actually got its start in a pre-Bridgerton world, thanks to a 2019 short film that garnered millions of views online. But I’m sure the breakout success of that Shondaland show didn’t hurt when it came to adapting Suzanne Allain’s source material into a full-length feature. Sope Dirisu is the dashing but hard-to-impress Mr. Jeremy Malcolm and Freida Pinto is the softspoken country lady who gets roped into a scheme to put him in his place. But it’s a comedic turn from Zawe Ashton that really steals the show in this gentle, genteel romance.

Win a Date with Tad Hamilton! (2004)

I can’t say Win a Date with Tad Hamilton! is particularly important to the overall rom-com canon, but it is important to the Caroline Siede personal rom-com canon so I thought it deserved a place here. This story of a big-time celebrity (Josh Duhamel) falling for a small-town girl (Kate Bosworth) was a favorite of mine in middle school—maybe because I was such a Topher Grace at the time. And when I revisited it for When Romance Met Comedy, I was pleased to discover that its retro throwback charms actually hold up pretty well. It’s got a winking, playful sense of self-awareness mixed with an earnest affection for rom-coms and those who love them.

Other stuff I’ve worked on lately: I gave a semi-rave to Netflix's new scammer drama Apple Cider Vinegar for The Boston Globe.