From romantic old Hollywood classics to hilarious new favorites, there's plenty to love about these titles on HBO Max. The 19 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.

The 19 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, Angela Andaloro, and James Mercadante

on August 19, 2025 05:56AM EDT

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 19 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.

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. *—Ilana Gordon*

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

Away We Go (2009)

John Krasinski as Burt and Maya Rudolph as Verona in 'Away We Go'.

Francois Duhamel/Focus

Like a lived-in sweatshirt, *Away We Go *is the kind of romantic comedy that becomes more beloved and comfortable over time. John Krasinski and Maya Rudolph star as Burt and Verona, a couple with a baby on the way and no idea where to settle down. After Burt's parents announce plans to move out of the country, Burt and Verona hit the road to visit family and friends, trying to decide where best to raise their child. The premise is simple, the characters are bold and specific, and Krasinski and Rudolph have an easy chemistry about them. The film is Rudolph at her comedic and dramatic best. *—I.G.*

Where to watch *Away We Go*: HBO Max

**Director: **Sam Mendes

**Cast: **John Krasinski, Maya Rudolph, Jeff Daniels, Maggie Gyllenhaal, Allison Janney, Chris Messina, Catherine O'Hara, Paul Schneider

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 (read the review)

**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

**EW grade:** (Read the review)

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

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

He's Just Not That Into You (2009)

Ginnifer Goodwin as Gigi, Jennifer Aniston as Beth, and Jennifer Connelly as Janine in 'He's Just Not That Into You'. Everett Collection

*He's Just Not That Into You* is adapted from a dating self-help book and, as such, doesn't always do the best job in the character development department. *But*, if you're looking for a fun film that hits every genre trope and features some of the late-aughts' most beloved romantic leads, then you can't go wrong with this rom-com*. *The entire ensemble is solid, but EW's reviewer shouts out Drew Barrymore's performance as a single woman "frustrated — convincingly — by the technology of modern dating, which she correctly nails as a series of walls people hide behind. She makes that complaint a cry from the heart." *—I.G.*

Where to watch* He's Just Not That Into You*: HBO Max

**EW grade:** (Read the review)

**Director: **Ken Kwapis

**Cast: **Ben Affleck, Jennifer Aniston, Drew Barrymore, Jennifer Connelly, Kevin Connolly, Bradley Cooper, Ginnifer Goodwin, Scarlett Johansson, Kris Kristofferson, Justin Long

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+ (read the review)

**Director: **René Clair

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

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– (read the review)

**Director: **Steven Soderbergh

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

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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

**EW grade:** (Read the review)

**Director:** Joel Zwick

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

Notting Hill (1999)

Hugh Grant as William Thacker and Julia Roberts as Anna Scott in 'Notting Hill'.

Clive Coote/Universal

When it comes to '90s romantic comedies, *Notting Hill* checks every box. The film is set in a charming London neighborhood, stars Julia Roberts and Hugh Grant, and there's a klutzy meet cute and an eccentric/charming best friend (Rhys Ifans) who can be relied upon for lighthearted laughs. What distinguishes *Notting Hill *from other films in the genre is the role reversal: Here, the woman is the powerful, successful catch and the man is the one fumbling over himself to keep her attention.

Roberts plays Anna Scott, a beloved American actress who stumbles upon a nerdy British bookstore clerk (Grant) and ends up liking him enough to hang around and meet his quirky circle of friends and family. An odd couple comedy about a privileged star who has everything but privacy and the normal guy who woos her with his everyday charm, *Notting Hill *is the perfect film for those who loved *Four Weddings* *and a Funeral* or *America's Sweethearts*. *—I.G.***

Where to watch *Notting Hill*: HBO Max**

**EW grade: **A– (read the review)**

**Director:** Roger Michell **

**Cast:** Julia Roberts, Hugh Grant, Hugh Bonneville, Emma Chambers, James Dreyfus, Rhys Ifans, Tim McInnerny, Gina McKee

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

**EW grade: **A (read the review)

**Director: **Joe Wright

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

Scott Pilgrim vs. the World (2010)

Michael Cera as Scott Pilgrim and Jason Schwartzman as Gideon Graves in 'Scott Pilgrim vs. the World'. Everett Collection

How hard are you willing to fight for love? For 22 year old musician Scott Pilgrim, the answer is very. After meeting and falling for Ramona Flowers, Scott discovers that to win her hand, he must first defeat her seven evil exes in combat. A romantic action comedy film based on the graphic novel series and told using videogame and comic-like imagery, *Scott Pilgrim vs. the World *may have Sex Bob-Ombed at the box office, but the film has since developed a loyal cult following — and rightly so.

With an ensemble cast featuring some of the best twentysomething comedic talent the early-2010s had to offer, *Scott Pilgrim* is a unique comedy with a style that's all its own. *—I.G.*****Where to watch *Scott Pilgrim vs. the World*: HBO Max******Director: **Edgar Wright******Cast: **Michael Cera, Mary Elizabeth Winstead, Kieran Culkin, Anna Kendrick, Alison Pill, Brandon Routh, Aubrey Plaza, Jason Schwartzman, Johnny Simmons, Chris Evans

Sex and the City: The Movie (2008)

Kristin Davis as Charlotte York, Sarah Jessica Parker as Carrie Bradshaw, Cynthia Nixon as Miranda Hobbes, and Kim Cattrall as Samantha Jones in 'Sex and the City: The Movie'.

New Line Cinema

After spending six seasons either loathing or swooning over Carrie Bradshaw's (Sarah Jessica Parker) will-they-won't-they relationship with Mr. Big (Chris Noth), loyal *Sex and the City* viewers were gifted a feature film four years post-series finale to meet their curiosity. In this cinematic continuation, the ever-pensive Big ruffles Carrie's feathers by jilting her at the altar, thus prompting the N.Y.C. writer to turn her pre-booked Mexico honeymoon into a healing journey by traveling with her three besties: Miranda (Cynthia Nixon), Samantha (Kim Cattrall), and Charlotte (Kristin Davis).

One of the highest-grossing rom-coms of all time, *Sex and the City: The Movie *is escapist fiction at its zenith, preserving the irresistible charm of the original series while injecting more melodrama, more luxury, more character development (albeit controversial), bigger and better closets, and — you guessed it — more sex. *—James Mercadante*

Where to watch *Sex and the City: The Movie*: HBO Max

**EW grade:** B+ (read the review)

**Director:** Michael Patrick King

**Cast:** Sarah Jessica Parker, Kim Cattrall, Kristin Davis, Cynthia Nixon, Jennifer Hudson, Candice Bergen, Chris Noth, David Eigenberg, Jason Lewis **

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 (read the review)

**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

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