Fall in love with the 10 best rom-coms on HBO Max

Looking to stream something romantic, but with a humorous tone? HBO Max has got you covered.

The streaming service’s expansive library features many longtime swoon-worthy favorites as well as modern romantic film classics. From teen movies to romantic musicals, we’re here to highlight some of the biggest rom-coms across the decades.

Here are the 10 best rom-coms on HBO Max that you can stream with your sweetheart this weekend.

1. When Harry Met Sally

A man and woman crouch down in front of a window.

A movie love story that might make you “ohhhhhhh”
Credit: Castle Rock / Nelson / Columbia / Kobal / Shutterstock

Billy Crystal and Meg Ryan star in this classic romantic comedy about two University of Chicago grads who meet on a drive to New York City together. Though the pair debate about whether a man and a woman can ever be “just friends” upon their meeting, they’re forced to confront this question many times as they bump into one another over a 12-year period.

When Harry Met Sally is timeless and feel-good, blending the realities of city romance with the fantasy of falling for a friend. Plus: I’ll have what she’s having.

How to watch: When Harry Met Sally is now streaming on HBO Max.

2. 13 Going on 30

A fanciful coming-of-age story about a girl who escapes the social pressures of junior high by turning 30 overnight? It sure sounds like a blast.

13 Going on 30 is one of those films that’s hard to forget because it’s just so fun. It has colorful costumes, memorable dance numbers, and an amusing story. Not to mention, Jennifer Garner and Mark Ruffalo make some fine childhood-friends-turned-lovers.

How to watch: 13 Going on 30 is now streaming on HBO Max.

3. Crazy Rich Asians

A man and woman sit at a bar

‘Crazy  Rich Asians’ is a romantic film worth watching over and over.
Credit: Warner Bros / Kobal / Shutterstock

Crazy Rich Asians revitalized the rom-com genre upon its release in 2018. Based on the best-selling book of the same name by Kevin Kwan, the story follows Chinese-American professor Rachel (Constance Wu), who travels to Singapore with her boyfriend, Nick (Henry Golding), for a wedding only to discover that his family is one of the wealthiest in the country. Rachel is also forced to confront Nick’s traditional mother who believes she is not good enough to marry her son.

With dazzling visuals and snappy writing, this one is definitely worth revisiting.

How to watch: Crazy Rich Asians is now streaming on HBO Max.

4. Clueless

Is there a better adaptation of Jane Austen’s Emma? As if!

Writer/director Amy Heckerling took the framework of that classic Regency-era romance and brilliantly translated it into 1995 Beverly Hills. There, the affluent, educated-yet-naïve Cher Horowitz (Alicia Silverstone) is the benevolent queen bee of her high school. Her acts of kindness include giving a glam makeover to the scruffy new girl (Brittany Murphy), donating skis to the poor, and matchmaking teachers and teens alike.

However, when it comes to her own love life, she is comically clueless. Slapstick, high-school hijinks, and shady one-liners make up much of the hilarious humor at play in this teen rom-com. On top of all that, there’s scads of style, from a parade of enviable outfits to a sensational soundtrack full of ‘90s bangers. But what makes Clueless a classic is how marvelously Silverstone grounds this heightened world with her winsome charm. — Kristy Puchko, Deputy Entertainment Editor *

How to watch: Clueless is now streaming on HBO Max.

5. Singin’ in the Rain

Two men and a woman sing together.

A singalong movie you’ll fall in love with.
Credit: Moviestore / Shutterstock

Though Singin’ in the Rain is approaching its 70th birthday, it remains one of the most iconic films in its genre.

The musical catches up with film star Don (Gene Kelly) and chorus girl Kathy (Debbie Reynolds) as they get caught up in the transition from silent films to those with sound. Because Don’s longtime romantic movie partner Lina (Jean Hagen) is not a skilled singer, Kathy is hired to record her voice over Lina’s image. However, this causes tension to brew in Hollywood.

How to watch: Singin’ in the Rain is now streaming on HBO Max.

6. 27 Dresses

This masterpiece penned by Crazy Ex-Girlfriend and The Devil Wears Prada’s Aline Brosh McKenna is a distinct high point in the rom-coms of the early aughts. Katherine Heigl stars as Jane, a hopeless romantic who has been a bridesmaid 27 times and starts to lose hope when the boss (Edward Burns) she’s secretly in love with starts dating her sister (Malin Åkerman). It doesn’t help that she’s being pestered by wedding columnist Kevin Doyle (James Marsden), who turns out to be exactly the kind of cynic Jane can’t stand, but we as viewers recognize as a delicious and inevitable enemies-to-lovers trope. 

McKenna and Anne Fletcher expertly dodge the casual misogyny and slut shaming of the times to achieve what so many romantic comedies (written and directed by men) do not. The sisters’ relationship is appropriately complicated and imbalanced, showing us Jane’s lonely suffering as well as its destructive power. Others may chide her love of love (including iconic horny BFF Judy Greer), but they know that it’s a strength, not a weakness — even Kevin, who becomes just right right kind of charming jerk in Marsden’s hands. — Proma Khosla, Senior Entertainment Reporter

How to watch: 27 Dresses is now streaming on HBO Max. 

7. You’ve Got Mail

A man and woman wait in a customer service line

‘You’ve Got Mail’ is such an intensely ’90s film.
Credit: Brian Hamill / Warner Bros / Kobal / Shutterstock

In the early days of the internet — before the world became flooded with dating apps — there was AOL Instant Messenger. This is how small bookstore owner Kathleen Kelly (Meg Ryan) anonymously meets Joe Fox (Tom Hanks), a man whose family owns a giant bookstore chain, in this ’90s rom-com. While the two flirt with one another online, their dislike of each other in real life threatens to get in the way of a blossoming romance.

Although we’re still mourning the cooperate takeover of Kathleen’s bookstore, You’ve Got Mail features a surprisingly well-rounded female lead, especially considering the decade it was released in. Also, who doesn’t love Tom Hanks? It’s an all-time classic film for a reason.

How to watch: You’ve Got Mail is now streaming on HBO Max.

8. Moonstruck

Cher won an Oscar for her lead role as Loretta in this operatically unhinged New York romantic comedy. A young widow who’s about to settle for a nice man she doesn’t really love until she meets his brother — the furious, wildly romantic Ronny (a 24-year-old Nicolas Cage, all raw angles and hangdog looks). John Patrick Shanley’s script is dry and giddy and wise, and will make anyone with a big, loud, nosy family full of loving pessimists feel seen. — Caitlin Welsh, Australia Editor *

How to watch: Moonstruck is now streaming on HBO Max.

9. My Big Fat Greek Wedding

A woman in a wedding gown and a man in a tuxedo sit in the back seat of a car

Break out the Windex and fall in love with this film.
Credit: Moviestore / Shutterstock

My Big Fat Greek Wedding is just as loud, energetic, and sweet as you remember.

The sleeper movie hit has 30-year-old Toula (Nia Vardalos) meeting the handsome Ian Miller (John Corbett) one day while waiting tables at her family’s Chicago restaurant. The pair reconnects after Toula begins working for a travel agency, and it’s not long before Ian puts a ring on her finger. Unfortunately for Toula, before the wedding can happen, Ian must get the approval of her giant, overbearing Greek family.

How to watch: My Big Fat Greek Wedding is now streaming on HBO Max.

10. A Cinderella Story

We have so much to thank A Cinderella Story for that it’s hard to even know where to begin. Is it the rain-soaked kiss between Hilary Duff and Chad Michael Murray? Is it Regina King’s speech about never letting the fear of striking out keep you from the game? Is it Jennifer Coolidge holding a cookie and saying, “so moist”? Regardless, this is an aughts film for the ages — one that takes the classic Cinderella story and adds so many great scenes you almost forget it’s based on anything. — Alison Foreman, Entertainment Reporter *

How to watch: A Cinderella Story is now streaming on HBO Max.

Asterisks (*) indicate the entry has been modified from a previous Mashable list.

Read more: mashable.com

  • February 5, 2022
  • NEWS