10 Best Rom-Coms To Stream On Valentine’s Day

Whether it's a romantic date night or a girls' night-in, HBO Max has the perfect movie for this Valentine's Day. Featuring timeless classics like Say Anything and Clueless to more modern movies filled with laughs and a tip of the hat to the classics like Easy A, there's no shortage of great romantic comedies on this streaming service.

Rom-coms are popular because they're familiar, containing timeless tropes people love to watch again and again. Valentine's Day is an excuse to be cheesy and watch a nostalgic love story starring beloved actors, preferably filled with laughter, and maybe the chance to shed some tears along the way.

She's All That

She's All That features a star-studded cast including Freddie Prinze Jr., Paul Walker, Matthew Lillard, and even a cameo from a baby-faced Usher. This flick from the '90s provides the ultimate trope of turning a nerd girl into a prom queen for a bet and ending up catching feelings along the way.

Laney is the total opposite of popular guy Zack Siler, not needing the drama that comes with being a popular girl in high school. When Zack bets his friend (Paul Walker) that he can make Laney prom queen, he comes to realize that maybe she's right and it's better to be happier for yourself rather than be what someone else wants them to be. There's plenty of reason for She's All That to be labeled a classic, as it's a fun, familiar storyline, with the ultimate (though maybe obvious) happy ending.

Clueless

One of the most notorious teen comedies of the '90s, Clueless, is filled with iconic quotes and fashion. Alicia Silverstone plays Cher, the popular girl in high school, who just as the title says, is a little clueless about life. Throughout the film, Cher thinks she knows everything there is to know about love and matchmaking, but when it comes to getting the hot new guy in school to like her she learns maybe she doesn't know as much as she thought.

There are some aspects of Clueless that didn't age well, like the fact that she ends up falling in love with her former step-brother, but the movie provides so many positives that the negatives are easy to overlook. Any lover of nostalgia and rom-coms is bound to have Clueless as a top contender.

Easy A

An ode to The Scarlet Letter and classic '80s teen movies, Easy A is bound to be a fun watch for the upcoming holiday. Emma Stone provides a refreshing take on a quirky teen girl learning just how quickly someone's reputation can become tainted.

This movie is loaded with quotable moments and laugh-out-loud scenes as viewers watch Olive embrace her new racy personality. She's a girl just looking for love, a hopeless romantic waiting for a guy to woo her like the good old days portrayed in the films written by John Hughes. Her relatable personality and the closeness of her family provides a storyline that makes for a great watch from start to finish.

Say Anything

Valentine's Day wouldn't be right without watching this classic rom-com starring John Cusack and Ione Skye. Lloyd (Cusack) falls in love with the valedictorian and is determined to be with her, much to the disappointment of the teen girl's father. The movie centers around their budding romance the summer before Diane (Skye) leaves for college, navigating life after graduation and the uncertainties of growing up it can come with.

Everyone remembers the iconic scene where Lloyd comes to Diane's house and holds up the boombox over his head, playing the song, "In Your Eyes" by Peter Gabriel. The scene has been watched and rewatched for decades, and that is why this movie goes down as one of the most nostalgic feel-good rom-coms from the '80s.

A Cinderella Story

This movie is perfect for the dreamers, as Hilary Duff portrays Sam, an aspiring writer with the dream to go to Princeton after high school. The film provides a modern-day fairy tale with not-so-subtle nods to the Disney movie Cinderella with Sam's less-than-perfect stepmother as well as her fairy-godmother equivalent at the diner she works at. The awkward girl gets her fairytale moment when she goes to the prom and dances with the cutest guy in school, who is oblivious to who he's dancing with because of a masquerade mask.

With Chad Michael Murray as the love interest and plenty of quotable moments, this film is guaranteed to warm every viewers' heart. This "original" Cinderella story inspired many sequels, but the classic stands up as the best of its kind.

How to Be Single

How to Be Single is the perfect movie for women who celebrate Galentine's Day. The film follows conventional rom-com tropes in an unconventional way and shows something romantic comedies don't always have the audacity to do—that women can be happy on their own.

The numerous plotlines and loveable characters throughout provide a light-hearted watch as Alice breaks up with her boyfriend to focus on her new life and career in New York City. It's a wonderful look at figuring out adulthood and how the support from others can make the leap of independence not as overwhelming.

27 Dresses

Katherine Heigl plays Jane, a woman who is always the bridesmaid and never the bride and has been in 27 weddings. She's in love with her boss, but too afraid to make her move, and her attractive baby sister swoops in and steals him from her. Along the way, Jane meets a guy named Kevin (played by James Marsden) who challenges her to stand up for herself and not be afraid to prioritize her own happiness, rather than try so hard for everyone else.

27 Dresses doesn't disappoint as the chemistry of Marsden and Heigl emanates from the screen, filling everyone with butterflies watching the two fall for each other. The humor throughout and the happy ending is the perfect formula.

The Wedding Singer

Adam Sandler and Drew Barrymore star in this classic '90s movie set in 1985. Sandler plays Robbie, the wedding singer, and Drew is a waitress at some of the events he sings for. The two realize that maybe they're dating the wrong people, which is confirmed when Robbie is left standing alone at the altar on his wedding day.

Robbie then realizes his feelings for Julia (Barrymore) and has the grand idea to stop her from marrying her cheating fiancé. The obvious chemistry the two have together and the classic storyline, as well as all of the great music, makes The Wedding Singer a fan-favorite romantic comedy.

13 Going On 30

This rom-com goes down as one of the best in history. Whether it's the outfits, the soundtrack, the cast, and the plot, there's nothing not to love about 13 Going On 30. A teenage girl makes a wish on her thirteenth birthday to be "thirty, flirty, and thriving," after being tired of being made fun of for being the awkward girl with only one friend.

Jennifer Garner makes Jenna come to life on screen, providing many hilarious moments as she wakes up and finds herself an adult, but with the same mindset as her thirteen-year-old self. The movie is a pleasant reminder that although growing up may have its perks, it's important not to age too fast.

Two Weeks Notice

Sandra Bullock plays an eccentric yet intelligent lawyer determined to save the local community center from being demolished. In the movie, she is offered a job by George (Hugh Grant), who is the exact opposite of Bullock as a rich, businessman with a habit of sleeping with the women he hires.

It's the actors' witty humor and sharp back and forth that make for this a great romantic comedy film. Two Weeks Notice follows another antiquated rom-com formula of two people totally opposite from one another realizing that opposites do, in fact, attract.

NEXT: 10 Best Movies For Valentine's Day If You Hate Rom-Coms