From romantic old Hollywood classics to hilarious new favorites, there's plenty to love about these titles on HBO Max. The 18 best romantic comedies on HBO Max From romantic old Hollywood classics to hilarious new favorites, there's plenty to love about these titles on HBO Max. By Ilana Gordon and Angela Andaloro on November 10, 2025 8:50 a.m. ET :maxbytes(150000):stripicc()/BestRomanticComediesonHBOMax100625bd4757dc3ca643a79b9c834aa2da67bf.

From romantic old Hollywood classics to hilarious new favorites, there's plenty to love about these titles on HBO Max.

The 18 best romantic comedies on HBO Max

From romantic old Hollywood classics to hilarious new favorites, there's plenty to love about these titles on HBO Max.

By Ilana Gordon and Angela Andaloro

on November 10, 2025 8:50 a.m. ET

Drew Barrymore as Lucy Whitmore in '50 First Dates'; Meryl Streep as Jane Adler and Alec Baldwin as Jake Adler in 'It's Complicated'; Ben Whishaw as the Limping Man and Colin Farrell as David in 'The Lobster'. Credit:

Darren Michaels/Columbia; Melinda Sue Gordon/Universal; Film4

If you're looking to fall in love from the comfort of your couch, HBO Max has you covered.

From screwball situations to sweet serenades, relationships come in many shapes and life stages, and these 18 HBO Max favorites will carry you from meet-cute to matrimony. Featuring films about platonic love, romantic love, and learning to love oneself, the movies on this list contain multitudes. Turn them on and they'll show you how to live, laugh, and love in ways a sign from T.J. Maxx could never.

50 First Dates (2004)

Drew Barrymore as Lucy Whitmore and Adam Sandler as Henry Roth in '50 First Dates'. Columbia/Courtesy Everett Collection

Six years after Adam Sandler and Drew Barrymore teamed up for *The Wedding Singer*, the two connected on screen for a second time, playing opposite each other in this daffy romantic comedy. Following a commitment-phobic veterinarian (Sandler) who falls in love with an artist suffering from short-term amnesia (Barrymore), *50 First Dates* hones in on and heightens the game of finding the person you can't stop thinking about — and dealing with the reality that they'll never remember meeting you.

Set on the island of Oahu — a location so consistently beautiful that it alone negates the idea of time passing — this premise-driven comedy finds emotional resonance amidst all the silly gags. Barrymore and Sandler have just as much chemistry together as they did in their first film, leading what EW's critic describes as "an agreeably deranged romance with a geeks-in-paradise Hawaiian setting." *—Ilana Gordon *

Where to watch *50 First Dates*: HBO Max

**Director: **Peter Segal

**Cast:** Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin, Dan Aykroyd

Am I OK? (2022)

Dakota Johnson as Lucy in 'Am I OK?'.

A coming out and coming-of-middle-age movie co-directed by comics and real-life spouses Tig Notaro and Stephanie Allynne, *Am I Ok? *is the queer millennial movie you didn't know you needed. Dakota Johnson stars as Lucy, a woman stuck in career and romantic limbo, who is forced out of her everyday mundanity by a new understanding of her sexuality and her best friend's upcoming international move.

A comedy about love — both platonic and romantic — the movie was filmed during the pandemic and premiered at Sundance, but has since found a home on HBO Max, and a fan base amongst movie lovers who enjoy authentic comedies about late bloomers finding love and themselves. *—I.G.*

Where to watch *Am I OK?*: HBO Max**

**Directors: **Tig Notaro, Stephanie Allynne

**Cast: **Dakota Johnson, Sonoya Mizuno, Jermaine Fowler, Kiersey Clemons, Molly Gordon, Whitmer Thomas, Odessa A'zion, Sean Hayes, Tig Notaro

Better Off Dead (1985)

John Cusack as Lane Meyer in 'Better Off Dead'.

A product of its time, *Better Off Dead* is an '80s romantic comedy about Lane Meyer (John Cusack), a teenager who decides the only cure for his broken heart is to end it all. Lane's pursuit of an Earthly exit, however, is interrupted when he meets a French exchange student who helps him get his groove back and motivates him to challenge his ex's new boyfriend to a high-stakes ski race.

A black comedy through and through, *Better Off Dead* gets its lifeblood from Cusack's charismatic performance of a depressed teen, and from the eccentric group of supporting characters who seem intent on making Lane's life harder and weirder. The movie has its moments that feel extra '80s, but as a former EW correspondent writes, *Better Off Dead*, "has the rare mix of heart and smarts to render it nearly timeless." *—I.G.*

Where to watch *Better Off Dead*: HBO Max

**Director:** Savage Steve Holland

**Cast: **John Cusack, David Ogden Stiers, Diane Franklin, Kim Darby

Casablanca (1942)

Humphrey Bogart as Rick Blaine and Ingrid Bergman as Ilsa Lund in 'Casablanca'. Everett Collection

Despite boasting some of the best quotes in all of cinematic history, *Casablanca* was just one of many films churned out by the studio system in the early years of World War II. But something about the movie's heart-wrenching love triangle, political and social relevance, and lush setting charmed viewers, propelling the project to an unexpected Best Picture win, and a permanent spot on almost every Best Of list.

Electricity rations were common at the time of the movie's release, but entirely unnecessary — the sexual currents pulsating between stars Humphrey Bogart and Ingrid Bergman had to have been strong enough to generate power for a small city, at the very least. *—I.G.*

Where to watch *Casablanca*: HBO Max

**EW grade:** A

**Director: **Michael Curtiz

**Cast: **Humphrey Bogart, Ingrid Bergman, Paul Henreid, Claude Rains

City Lights (1931)

Charlie Chaplin as the Tramp and Virginia Cherrill as the Blind Girl in 'City Lights'.

Courtesy Everett

HBO Max offers a number of Charlie Chaplin's movies, features and shorts — the actor, director, and composer made 81 throughout the course of his career — but *City Lights *shines brighter than most. Released in 1931, a few years after "talkies" began overtaking theaters, Chaplin chose to limit *City Light's *sound to its score. But even without dialogue, this romantic comedy creates an emotional vibe that an EW critic called a "consummate weeper."

Chaplin returns as the Little Tramp, his signature character, who falls in love with a young blind woman. When the woman mistakes him for a millionaire, the Tramp befriends an actual millionaire and hopes to use his money to pay for an operation that would restore the woman's sight. The movie is a must-see for any comedy or cinema history enthusiast. —*I.G.*

Where to watch *City Lights*: HBO Max

**Director: **Charlie Chaplin

**Cast: **Charlie Chaplin, Virginia Cherrill, Florence Lee, Harry Myers, Al Ernest Garcia

Dinner With Friends (2001)

Toni Collette as Beth, Dennis Quaid as Gabe, Greg Kinnear as Tom, and Andie MacDowell as Karen in 'Dinner With Friends'. Everett

HBO Max's cinematic adaptation of Donald Margulies' Pulitzer Prize winning 1998 play, *Dinner With Friends *maintains the original's simple premise while mining deep for emotional and personal revelations. The story of two New England couples dealing with the fact that one of the pairs is divorcing, the film captures the unexpected moments of vulnerability and honesty that define long-term relationships — even ones that are falling apart.

Dennis Quaid and Andie MacDowell are perfectly cast as a pair of foodies who are more comfortable navigating what's on their dinner plates than what's going on in their friends' lives, and Greg Kinnear and Toni Collette toggle between insecurity and self-assurance as the couple whose marriage is broken up by an affair with a younger woman. Haute cuisine served over seven scenes, *Dinner With Friends *is the rare adaptation that remains faithful to the original while still finding new paths to tread. *—I.G.*

Where to watch *Dinner With Friends*: HBO Max

**Director: **Norman Jewison** **

**Cast: **Dennis Quaid, Andie MacDowell, Greg Kinnear, Toni Collette

I Married a Witch (1942)

Frederic March as Wallace and Veronica Lake as Jennifer in 'I Married a Witch'.

Donaldson Collection/Getty

Fans of the '60s sitcom *Bewitched *might want to check out *I Married a Witch*, a romantic comedy whose lighthearted absurdism was likely intended to serve as a distraction from the violence happening overseas during the Second World War.

Veronica Lake stars as Jennifer, a witch who returns to Earth centuries after being burned at the stake, seeking revenge against the descendant of Jonathan Wooley, the Puritan who persecuted her. But her plans for retribution are rerouted after Jennifer meets Wallace Wooley, an aspiring politician, and falls in love with him. All of the Wooley men in the movie are portrayed by Fredric March, but it's Lake's wit and charisma that carry the film. *—I.G.*

Where to watch *I Married a Witch*: HBO Max

**EW grade: **B+

**Director: **René Clair

**Cast: **Fredric March, Veronica Lake, Robert Benchley, Susan Hayward, Cecil Kellaway

It's Complicated (2009)

Meryl Streep as Jane Adler and Steve Martin as Adam Schaffer in 'It's Complicated'.

Melinda Sue Gordon/Universal/Courtesy Everett

You can expect three things from a Nancy Meyers film: romance, comedy, and superior kitchens. The Meyers trifecta is on full display in *It's Complicated*, a movie that EW's critic at the time referred to as "middle-aged femme porn." Meryl Streep stars as Jane Adler, a successful bakery owner whose amicable relationship with her ex-husband, Jake (Alec Baldwin), takes a detour back into the romantic after a decade apart.

A broad comedy distinguished by its excellent cast and focus on romanticizing the love and sex lives of middle-aged people,* It's Complicated* keeps its story and message simple. And by doing so in such an aesthetic and well-executed style, it feels like a real treat. *—I.G.*

Where to watch *It's Complicated*: HBO Max

**Director: **Nancy Meyers

**Cast:** Meryl Streep, Alec Baldwin, Steve Martin, John Krasinski, Lake Bell

The Last of the Blonde Bombshells (2000)

Billie Whitelaw as Evelyn and Judi Dench as Elizabeth in 'The Last of the Blonde Bombshells'. HBO/Everett

A film with a sensibility that can only be described as singularly British, *The Last of the Blonde Bombshells *is a romantic comedy with some rhythm. Elizabeth (Judi Dench) spent World War II playing saxophone in a swing band called the Blonde Bombshells. After the death of her husband, Elizabeth reconnects with Patrick (Ian Holm) — the band's former drummer and only male member, who avoided conscription during the war by cross-dressing.

When the pair start dating, Elizabeth decides to get the band back together, but discovers the Bombshells have scattered with members in jail, suffering from alcoholism, and devoted to the Salvation Army. Witty and nostalgic, *The Last of the Blonde Bombshells *is another piece of evidence that blondes really do have more fun. *—I.G.*

Where to watch *The Last of the Blonde Bombshells*: HBO Max

**Director: **Gillies MacKinnon** **

**Cast: **Judi Dench, Ian Holm, Romola Garai, Olympia Dukakis

Love & Other Drugs (2010)

Anne Hathaway as Maggie Murdock and Jake Gyllenhaal as Jamie Randall in 'Love & Other Drugs'.

Twentieth Century Fox Film Corporation/Courtesy Everett Collection

Five years after playing a married couple in the cowboy drama *Brokeback Mountain*, Jake Gyllenhaal and Anne Hathaway reunite to play opposite each other in *Love & Other Drugs*. A romantic comedy that lets it all hang out — both physically and emotionally — the film follows a pharmaceutical sales representative (Gyllenhaal) who falls in love with a free spirit afflicted with an incurable disease (Hathaway). Based on Jamie Reidy's 2005 non-fiction book *Hard Sell: The Evolution of a Viagra Salesman*, the film traffics in ideas about love, sex, sickness, health, medical ethics, and the brokenness of America's healthcare system.

Generally known for his more dramatic roles, Gyllenhaal gets a chance to show off his comedic chops through his character, the ethically dubious ne'er-do-well Jamie, and his and Hathaway's chemistry is more alive than it was in *Brokeback Mountain*. The film's nudity and sex scenes are intimate and effective, but side effects include discomfort when watching with the whole family. *—I.G.*

Where to watch *Love & Other Drugs*: HBO Max

**Director: **Edward Zwick

**Cast: **Jake Gyllenhaal, Anne Hathaway, Oliver Platt, Hank Azaria, Josh Gad, Gabriel Macht

Let Them All Talk (2020)

Meryl Streep as Alice in 'Let Them All Talk'. HBO Max

Joan Didion once said "Writers are always selling someone out," and that is exactly what Pulitzer Prize-winning author Alice Hughes (Meryl Streep) is accused of doing. In *Let Them All Talk*, Alice boards the Queen Mary 2 on a transatlantic trip with the intention of writing her new book and spending time with two of her oldest friends (Candice Bergen and Dianne Wiest). But as the voyage proceeds, Alice ends up battling with Roberta (Bergen) over how much of her original book was based on Roberta's life, and watching as her nephew Tyler (Lucas Hedges) falls for her literary agent, Karen (Gemma Chan).

Funny, wise, bitter, primarily improvised, and made in barely two weeks, EW's critic describes the film as "a chance to spend two hours watching Streep & Co. make the most of Deborah Eisenberg's deliciously salty script, while Soderbergh — who also serves as cinematographer — shoots it all in ruthless, radiant light." *—I.G.*

Where to watch *Let Them All Talk*: HBO Max

**EW grade: **A–

**Director: **Steven Soderbergh

**Cast: **Meryl Streep, Candice Bergen, Dianne Wiest, Gemma Chan, Lucas Hedges

16 swoon-worthy romantic comedies to watch on Hulu right now

The 20 best romantic comedy movies on Netflix

The Lobster (2015)

Jessica Barden as Nosebleed Woman and Colin Farrell as David in 'The Lobster'.

Everett Collection

An absurdist black comedy that satirizes our culture's discomfort around uncoupled people, *The Lobster* asks what would happen if singles were given 45 days to find a mate, or be transformed into the animal of their choice. After David's (Colin Farrell) wife leaves him, he is taken to a hotel and instructed to find someone compatible. But when an incident involving a potential life partner forces him to flee into the woods to live with the loners, David discovers that it doesn't matter where you are or who you're with — falling in love is never easy. *The Lobster* is one of the most original romantic comedies, and will live in your brain rent-free for weeks after watching. *—I.G.*

Where to watch *The Lobster*: HBO Max

**EW grade: **A

**Director: **Yorgos Lanthimos

**Cast:** Colin Farrell, Rachel Weisz, Ben Whishaw, John C. Reilly, Olivia Colman, Léa Seydoux

My Big Fat Greek Wedding (2002)

John Corbett as Ian Miller and Nia Vardalos as Toula Portokalos in 'My Big Fat Greek Wedding'. Gold Circle Films

Toula Portokalos (Nia Vardalos) embraces her role as the loyal yet overlooked member of her enormous clan until she decides to take control of her life at 30. While her parents tirelessly seek the perfect Greek man for her, Toula knows none of those suitors stand a chance against WASP English teacher Ian Miller (John Corbett), who's head over heels for her and is ready to take on the challenge of getting her family to approve their marriage. (He's really all that and a bottle of Windex!)

Adapted from Vardalos' one-woman show based on her real-life family, *My Big Fat Greek Wedding *delves into the dynamics of growing up in an immigrant household deeply rooted in their culture, navigating a world that centers on conformity. —*Angela Andaloro*

Where to watch *My Big Fat Greek Wedding*: HBO Max

**Director:** Joel Zwick

**Cast:** Nia Vardalos, John Corbett, Lainie Kazan, Michael Constantine, Gia Carides, Louis Mandylor, Andrea Martin, Joey Fatone**

Pride & Prejudice (2005)

Matthew Macfadyen as Mr. Darcy and Keira Knightley as Elizabeth Bennet in 'Pride & Prejudice'.

Alex Bailey/Focus Features

It is a truth universally acknowledged that of all the film and TV adaptations of Jane Austen's acclaimed novel, first published in 1813, the 2005 version of *Pride & Prejudice* ranks among the top two. Long before Matthew Macfadyen battled for his place in the corporate hierarchy as *Succession*'s Tom Wambsgans, he matched wits with Elizabeth Bennet (Keira Knightley) as the apparently standoffish but ultimately well-intentioned Mr. Darcy (a role previously aced by Colin Firth in the 1995 TV drama).

A film that earned Knightley her first Oscar nod for Best Actress, the remake — directed by Joe Wright — infuses modern relevance into a beloved period piece. EW's review promises, "The acting in *Pride & Prejudice* tingles with nuance and presence." *—I.G.*

Where to watch *Pride & Prejudice*: HBO Max through Nov. 30

**EW grade: **A

**Director: **Joe Wright

**Cast:** Keira Knightley, Matthew Macfadyen, Brenda Blethyn, Donald Sutherland, Rosamund Pike, Carey Mulligan, Jena Malone, Talulah Riley, Simon Woods, Rupert Friend

Silver Linings Playbook (2012)

Jennifer Lawrence as Tiffany Maxwell and Bradley Cooper as Pat Solitano in 'Silver Linings Playbook'.

Weinstein Company/Courtesy Everett Collection

Rarely is mental health explored on screen in a nuanced, vibrant, joyful way, but that's exactly the tone director David O. Russell nails in *Silver Linings Playbook*. Pat and Tiffany (Bradley Cooper and Jennifer Lawrence) are both dealing with personal issues and recovering from losing their romantic partners. Unmoored and filterless, they meet and agree to help each other out — Tiffany promises to assist Pat in winning back his ex-wife, and in turn, he agrees to be her partner in a dance competition.

As they rehearse together and struggle to sort through their woes, they uncover coping mechanisms that allow them to not only live but find the beauty in their respective challenges. The kind of entertaining movie that cleans up at awards shows while still retaining its rewatchability, EW's critic at the time writes, "We're ready for the comedy of craziness, but the depth of compassion is the movie's silver lining." *—I.G.*

Where to watch *Silver Linings Playbook*: HBO Max

**EW grade: **A

**Director:** David O. Russell

**Cast: **Bradley Cooper, Jennifer Lawrence, Robert De Niro, Jacki Weaver, Chris Tucker

Singin' in the Rain (1952)

Debbie Reynolds as Kathy Selden and Gene Kelly as Don Lockwood in 'Singin' in the Rain'. Everett Collection

Widely considered one of the best musicals ever captured on film, *Singin' in the Rain* has everything from music and dance to comedy and romance. Released 29 years after the entertainment industry premiered its first movie featuring sound-on-film, the story stars Gene Kelly as a celebrated silent film actor struggling to make the jump to the talkies, and Debbie Reynolds as an up-and-coming actress trying to break into the business.

The majority of the film's comedy and over-the-top dance numbers are provided by the charismatic Donald O'Connor, and Jean Hagen makes a delightful (and Oscar-nominated) turn as Lina, a silent movie star with a face for film and a Brooklyn accent strong enough to stop traffic. A beloved treasure and shining representative from Hollywood's Golden Era, *Singin' in the Rain* continues to endure and inspire. *—I.G.*

Where to watch *Singin' in the Rain*: HBO Max

**Directors: **Stanley Donen, Gene Kelly

**Cast: **Gene Kelly, Debbie Reynolds, Donald O'Connor, Jean Hagen

We Live in Time (2024)

Andrew Garfield as Tobias and Florence Pugh as Almut in 'We Live in Time'.

Peter Mountain/StudioCanal

A romantic dramedy about love, aging, and what it truly means to live life to the fullest, *We Live in Time* is a film told across three different timelines. From the moment Almut (Florence Pugh) and Tobias (Andrew Garfield) first meet — she hits him with her car as he's on his way to sign divorce papers — it's clear this film is not interested in employing a traditional, linear, narrative structure.

The movie jumps between past, present, and future, and while the logic for why the story moves the way it does isn't always clear, the characters, their relationship, and the chemistry between Pugh and Garfield is strong enough to ground the audience through the leaps. Director John Crowley tells EW that his film's ambition is to "hopefully capture the sense of what it feels like to be on the inside of a relationship." He pulls it off, and the result is charming. *—I.G.*

Where to watch *We Live in Time*: HBO Max

**Director: **John Crowley

**Cast: **Andrew Garfield, Florence Pugh

Your Monster (2024)

Tommy Dewey as Monster and Melissa Barrera as Laura Franco in 'Your Monster'.

A horror romantic comedy that riffs on *Beauty and the Beast*, *Your Monster* is a genre mash-up that is sure to delight. Laura (Melissa Barrera) has just been broken up with by her long-term boyfriend Jacob (Edmund Donovan). Forced to move back home, Laura discovers a monster (Tommy Dewey) squatting in her childhood bedroom. He agrees to give her two weeks to get her life together, and so begins the relationship between a woman trying to move on and the monster who lives in her closet.

Much of the film centers around a musical theater production involving Jacob, Laura, and the woman Laura believes Jacob is romantically interested in, so the film has some great production numbers. But the movie primarily exists as a showcase for Barrera, one of the most exciting actors in this new class of Scream Queens. *—I.G.*

Where to watch *Your Monster*: HBO Max

**Director: **Caroline Lindy

**Cast: **Melissa Barrera, Tommy Dewey, Edmund Donovan, Kayla Foster, Meghann Fahy

Original Article on Source

Source: "EW Movies"

Read More

---

Source: Movies

Published: November 10, 2025 at 07:38PM on Source: MARIO MAG

#ShowBiz#Sports#Celebrities#Lifestyle