As the weather gets warmer, you might find yourself in the mood to be swept off your feet with a bit of summer romance.
If that’s the case, head on over to Max, HBO and Warner Bros. Discovery’s premium streaming service, which hosts a surprising number of romantic comedies.
This month’s additions include a musical adaptation of a modern rom-com classic and a swashbuckling fantasy featuring one of the great romances of the last century.
Get swept off your feet with these swoon-worthy flicks in May!
Need more recommendations? Then check out the Best New Movies on Netflix, (HBO) Max, Hulu, Amazon Prime and More, the Best Movies on Amazon Prime Video Right Now, the Best Rom-Com Movies on Netflix Right Now and the 4 Underrated Movies on Netflix in April 2025.
This Broadway adaptation of the Keri Russell romantic dramedy has even more delicious heart than the original. When diner waitress and master pie baker Jenna (Sara Bareilles, who also wrote the music for the show) finds herself pregnant, she decides to save up and enter a pie contest to escape her abusive husband Earl (Joe Tippett). Her best friends Dawn (Caitlin Houlahan) and Becky (Charity Angél Dawson) encourage her along the way. But things get a little more complicated when, much to her surprise, she ends up having an affair with her kind and understanding OB/GYN, Dr. Pomatter (Drew Gehling).
Jenna’s pregnancy helps her discover strength she never imagined she had. The songs are irresistibly funny and catchy in one moment and heartbreakingly beautiful in the next. Waitress: The Musical will leave you hungry for more — and for a slice of pie.
To paraphrase one of the dozens of quotable lines in The Princess Bride, there’s a shortage of perfect movies in the world. It would be a pity to miss this one.
The Princess Bride is a practically perfect story, featuring fencing, fighting, horseback riding, “true love, miracles” and Rodents of Unusual Size. A framing device serves up the wonderful backdrop for this swashbuckling tale — a grandfather (Peter Falk) reading a story to his grandson (Fred Savage) while he’s home sick from school. Gramps shares the story of Buttercup (Robin Wright), a beautiful but spoiled maiden, and Westley (Cary Elwes), the farmboy who wins her heart.
When the evil Prince Humperdinck (Chris Sarandon) kidnaps Buttercup, Westley teams up with master swordsman Inigo (Mandy Patinkin) and giant Fezzik (André the Giant) to rescue his true love. It’s funny, charming and romantic. Not loving this movie is “inconceivable.”
He’s Just Not That Into You is based on a book, which is itself based on a line of dialogue from an episode of Sex and the City. The movie’s sprawling origin story feels relevant to its plot, which features a large ensemble cast of interconnected characters. Each couple (or trio or quartet) includes one person who is much more invested in the relationship than the other — an imbalance that almost any viewer can relate to.
The connective thread is Gigi (Ginnifer Goodwin), a hopeless romantic who is constantly pursuing disinterested men. When she meets Alex (Justin Long), an aloof bartender, he begins giving her advice about how to interpret signals from guys. Meanwhile, their friends and coworkers are stuck in their own romantic entanglements. The impressive cast includes Scarlett Johansson, Bradley Cooper, Jennifer Connelly, Ben Affleck, Jennifer Aniston, Drew Barrymore and Kevin Connolly.
ABBA + Meryl Streep + stunning Greek island vistas = perfection. This movie version of the jukebox musical is a sparkling, effervescent affair about Sophie (Amanda Seyfried), a young woman desperate to learn the identity of her father before her wedding to Sky (Dominic Cooper). But her mother Donna (Streep) doesn’t know exactly who Sophie’s father is. There are three candidates — Sam (Pierce Brosnan), Bill (Stellan Skarsgård) or Harry (Colin Firth). Certain that she’ll know her dad as soon as she meets him, Sophie invites all three men to the wedding.
What follows is a farcical romantic musical comedy full of stellar choreography, funny dialogue and a sweet message about true love — for a partner but also for yourself. Christine Baranski and Julie Walters are particularly delightful as Donna’s best friends and former bandmates who help her as she tries to balance her unexpected reunion with her three exes and her daughter’s upcoming nuptials.
Crazy Rich Asians was groundbreaking for the mainstream spotlight it placed on Asian (particularly Chinese) characters and actors. It features stars like Constance Wu, Michelle Yeoh, Gemma Chan and Awkwafina in a love story about class, wealth and culture.
Rachel (Wu) is a New York economics professor happily in love with Nick Young (Henry Golding). When Nick takes Rachel to Singapore for the wedding of his best friend, Rachel learns that Nick’s family is part of Singapore’s wealthy high society. Not only are Nick and Rachel constantly in the public eye, Nick’s mother Eleanor (Yeoh) has incredibly high expectations about who her son should marry. Rachel, as a middle-class American, meets none of those expectations.
Rachel has to fight for love and the future she wants in this movie, which features fantastic fashion, eye-catching settings and a soundtrack with music by Asian artists like Jasmine Chen. Rachel is an engaging, relatable protagonist who you’ll root for every step of the way.
A charming examination of love amid mental health issues, Silver Linings Playbook is a must-see romantic comedy that’s both heart-wrenching and heartwarming. Pat (Bradley Cooper) has recently completed a stint in a psychiatric facility after a violent episode when he caught his ex-wife Nikki (Brea Bee) cheating on him. Desperate to reconcile, Pat moves in with his parents, Patrizio Sr. and Dolores (Robert De Niro and Jacki Weaver).
He meets Tiffany (Jennifer Lawrence), a widow who is also dealing with mental health problems. She encourages Pat to compete with her in a ballroom dance contest to prove to Nikki that he’s changed. Unfortunately, Patrizio Sr.’s gambling problem and obsession with the Eagles cause him to pressure his son and drive a wedge between him and Tiffany. (Patrizio superstitiously believes Pat’s attention to Eagles games is necessary for the team to win.)
The tension is near constant in this pressure cooker of a movie, yet it still manages to deliver laughs. Lawrence, De Niro and Cooper make deeply flawed characters extremely likable, while the family dynamics are complex and relatable. If you’ve ever felt like your family is about to drive you off the deep end, this movie is for you.
Toula (Nia Vardalos) is a shy, awkward woman who has always felt like an outsider in her loud, effusive Greek American family. When she falls in love with WASP-y teacher Ian (John Corbett), she struggles to get her family to accept him. Throughout the movie, she learns to stand up for herself and the man she loves, but she also learns to appreciate the rich culture that makes her family unique. It’s a heartwarming, hilarious story.
Despite being over twenty years old, My Big Fat Greek Wedding remains the highest-grossing rom-com of all time — and rightfully so. The script, written by lead actress Vardalos, is instantly quotable and emotionally resonant. More importantly, Toula and Ian’s romance is endlessly endearing. The movie spawned two sequels in 2016 and 2023, but the original remains the best of the bunch.
Based on the bestselling 1996 novel, this sharp and hilarious rom-com follows Bridget Jones (Renée Zellweger), an ordinary “singleton” with a habit of ending up in ridiculously awkward situations, as she documents her quest for self-improvement in a wine-soaked diary. Caught between smug married friends and the pressures of turning 30, Bridget navigates the chaos of modern womanhood with humor and heart.
Things get even messier when she begins a flirtation with her charming scoundrel of a boss, Daniel Cleaver (Hugh Grant), and keeps crossing paths with the uptight but oddly endearing Mark Darcy (Colin Firth), who harbors an unexplained grudge against Daniel. Loosely inspired by Jane Austen’s classic novel Pride and Prejudice, Bridget Jones’s Diary is an entertaining chronicle of its title heroine’s journey of growth, misjudged first impressions and realizing that love rarely goes according to plan.
