Rom-coms are always a good idea and as Valentine’s Day approaches, there’s no better time to bring out the classics and indulge in some of the best love stories on screen. These movies offer the perfect mix of humor and heart, whether you’re watching them with a partner, friends or even solo. From iconic meet-cutes to unforgettable love stories, these are some must-watch rom-coms that embrace the messy, funny and imperfect sides of love.
“How to Lose a Guy in 10 Days” – Streaming on: Paramount+
Andie Anderson, played by Kate Hudson, is a witty and determined journalist tasked with finishing her famous “how-to” column by sabotaging a relationship in just ten days. Simultaneously, Ben Barry, a hot-shot executive and ladies’ man, played by Matthew McConaughey, bets he can make a woman fall for him in the same window. In their battle of conflicting motives, things begin to feel a little too real when unexpected feelings develop. A mix of undeniable chemistry, sharp banter and unforgettable scenes makes “How to Lose a Guy in 10 Days” a standout rom-com.
“Notting Hill” – Streaming on: Prime Video
“Notting Hill” is a classic rom-com showcasing an unlikely romance between two people from entirely different worlds. William Thacker, played by Hugh Grant, is a simple London bookstore owner. Anna Scott, played by Julia Roberts, is a famous American actress who stumbles into his shop one day and a series of fateful encounters, both awkward and sweet, transform into love. The story is centered on the couple as they navigate a relationship amid very different lifestyles. Featuring an iconic love declaration, meet-cute and classic romance tropes, “Notting Hill” is a defining film of the genre.
“Ten Things I Hate About You” – Streaming on: Disney+
Inspired by Shakespeare’s “Taming of the Shrew,” this film brings a classic story to a high school setting, perfectly balancing humor with passion and vulnerability. The film weaves two love stories but primarily follows the fiercely independent Kat, played by Julia Stiles, and charming bad boy Patrick, played by Heath Ledger, whose relationship begins as a dating scheme before transforming into something real. “Ten Things I Hate About You” is filled with unforgettable scenes like Patrick’s musical performance and Kat reciting her poem. At its core, the film explores romance, betrayal, independence and what it means to be an outsider.
“Crazy Rich Asians” – Streaming on: Prime Video
Unbeknownst to his longtime partner, Nick Young, played by Henry Golding, comes from a world of unimaginable wealth and luxury. When his girlfriend Rachel Chu, played by Constance Wu, accompanies him on a trip to his native home in Singapore, she discovers his opulent, over-the-top lifestyle and disapproving family. As his family and jealous acquaintances work to bring her down, Rachel must navigate this foreign world and solidify her relationship. Not only does this film tell the story of a blooming romance, it also explores identity, family expectations and the struggle of choosing personal happiness over social pressures. “Crazy Rich Asians” showcases striking visuals, hilarious scenes and offers Asian representation rarely seen in rom-coms.
“Clueless” – Streaming on: Paramount+
“Clueless” is chaotic, but one of the most influential rom-coms to date, and is loosely based on Jane Austen’s novel “Emma.” Confident and popular Cher, played by Alicia Silverstone, is her high school’s it-girl. Self-assured in her understanding of romance, she believes she is the ultimate matchmaker, taking on a new student as her next project. She gradually realizes she does not have everything figured out, finding herself with feelings for her ex-step-brother, Josh, played by Paul Rudd. “Clueless” is celebrated for its sharp humor and take on teen culture, privilege and character depth beyond surface-level personas.
“Crazy, Stupid, Love” – Streaming on: Netflix
“Crazy, Stupid, Love” follows an interconnected group of characters as they navigate love at its many stages. Wealthy and charismatic playboy Jacob Palmer, played by Ryan Gosling, takes middle-aged Cal, played by Steve Carell, under his wing after Cal’s marriage falls apart. As Jacob teaches Cal his methods, his approach is challenged when he unexpectedly finds himself catching feelings for Hannah Weaver, played by Emma Stone, who was initially meant to be a casual hookup. Through its parallel relationships, the film presents love in many forms and makes for a funny yet emotionally rich movie.
“The Holiday” – Streaming on: Prime Video
If you’re nostalgic for the Christmas season, “The Holiday” is the perfect mix of festive vibes and romance suited for any time. Two women from opposite sides of the world, both eager to escape the troubles of their lives, agree to swap homes for two weeks over Christmas. Californian Amanda, played by Cameron Diaz, and Englishwoman Iris, played by Kate Winslet, each find unexpected sparks as they navigate unfamiliar surroundings.
“50 First Dates” – Streaming on: Prime Video
Playboy Henry Roth, played by Adam Sandler, seriously fears commitment. Working as a veterinarian in Hawaii makes for the perfect setup to pursue tourists and avoid long-term relationships, until he meets Lucy Whitmore, played by Drew Barrymore. Unknown to Henry, Lucy suffered severe brain trauma causing her to experience short-term memory loss, forgetting everything after she falls asleep. Nonetheless, Henry is determined to make her fall for him again every day. While the story is humorous on the surface, it also showcases a heartfelt exploration of patience and what commitment truly means.
“13 Going on 30” – Streaming on: Tubi
“Thirty, flirty, and thriving” is the goal of 13-year-old Jenna Rink, played by Jennifer Garner, but when her wish suddenly becomes reality, she’s thrown into adulthood, forced to navigate relationships and growing up apart from her fantasies. The film’s romance revolves around Jenna reconnecting with her former childhood best friend, Matt, played by Mark Ruffalo, now as an adult. “13 Going on 30” reflects on adulthood, lost bonds and enduring love in a comedic and heartfelt package.
“She’s The Man” – Streaming on: Paramount+
Another Shakespearean spin-off, “She’s The Man,” presents a modern twist on the play “Twelfth Night.” This film is the perfect lighthearted, feel-good movie. Viola, played by Amanda Bynes, a passionate high school soccer player, takes matters into her own hands when her school’s girls’ team is cut. Eager to prove she’s just as good as the boys, Viola decides to disguise herself as her twin brother who is conveniently ditching the first weeks of school, and joins the boy’s soccer team at his elite boarding school. What she doesn’t expect is to fall in love with his roommate Duke, and end up in a messy relationship web amidst her multiple personas.
