10 Movies to Queue Up After Sierra Burgess Is a Loser

Like Sierra Burgess Is a Loser, A Cinderella Story revolves around an unpopular girl developing an e-relationship with a popular jock without him realizing her identity. This one is the ultimate millennial fave: Chad Michael Murray, Hilary Duff, flip phones, and instant messenger systems. It's one of those deliciously earnest, slightly cheesy mid-2000s comedies that we all love, not in spite of their corniness, but because of it.

If you're in the mood for a darker take on romantic manipulations, this classic teen drama is for you. Just as Sierra Burgess is loosely based on the play Cyrano de Bergerac, Cruel Intentions is the high-school version of Les Liaisons dangereuses. In this update, two popular step-siblings manipulate their classmates' love lives for their own purposes and entertainment. It's a soapy melodrama that takes a much darker view of the fake-relationship tropes that are such a staple of other, lighter rom-coms.

Teenagers aren't the only ones who pretend to be someone they're not. In this Sandra Bullock-led rom-com, Lucy saves a stranger whom she secretly has a crush on and is mistaken for his fiance. Just as Sierra Burgess can't bring herself to unravel the lie because she's developing real feelings, Lucy also doesn't want to reveal the truth after she comes to love the man's family (especially his brother).

Easy A is probably best known as the film that cemented Emma Stone's status as a bona-fide leading lady. It's also an iconic entry into the lie-that-grows-out-of-hand subgenre. Stone's character, Olive, lets a lie get out of hand about losing her virginity and soon finds herself branded as the school tramp — something she embraces at first but starts to regret. Like Sierra Burgess, it's about the struggle a character has to build real relationships while entangled in a big lie.

Comparisons between Netflix's recent teen rom-coms and the ultimate teen movie king, John Hughes, are inevitable. The whole popular-guy-and-unpopular-girl storyline is a staple of his films, but none more so than Pretty in Pink. Jamey, Noah Centineo's slightly dorky jock in Sierra Burgess Is a Loser, often resembles Blane, the soft-spoken rich guy who falls for Molly Ringwald's proud, working-class Andie. Happily-ever-afters abound, but only after some honesty on both sides.

While we're on the subject of teen-movie adaptations of classical theater, we've got to talk about 10 Things I Hate About You, the late-'90s high-school update of Shakespeare's The Taming of the Shrew. It's the movie that made everyone fall in love with Heath Ledger as Patrick, the self-centered bad boy who meets his perfect match in acid-tongued Kat, resulting in one of the most quotable movies ever made. The only problem, of course, is that he's been flirting with her under false pretenses in order to help the guy who wants to ask out Kat's sister. What could possibly go wrong?

If you've been obsessively rewatching Set It Up since it debuted on Netflix, you probably remember the conversation that Charlie and Harper have about whether they're "Parent Trapping" or "Cyrano-ing" their bosses. The Cyrano de Bergerac story hinges on an eloquent but unattractive man feeding lines to his attractive but inept friend to help him woo a woman, which isn't that far off from this tale of savvy, exhausted assistants puppeteering their overbearing bosses into a romance.

Could we do a rundown of romantic-manipulation movies without including this hilarious update of Jane Austen's Emma? Ugh, as if! The catch here is that our heroine Cher isn't trying to benefit her own love life but instead is trying to matchmake among her friends. Under Cher's guidance, her friend Tai convinces herself to fall for wildly inappropriate guys, until real feelings start to intrude for everyone involved.

Cross-dressing comedies go back even further than Shakespeare (which, incidentally, She's the Man is based on), and while they're not as popular today, this 2006 Amanda Bynes/Channing Tatum comedy is definitely an old favorite. Viola passes herself off as her twin brother, Sebastian, so that he can go to London with his band. While disguised as her brother, Viola accidentally gets wrapped up in a love triangle between her roommate (and crush) Duke and the girl he likes, Olivia. And things only get more complicated when the real Sebastian turns up earlier than expected . . .

Secret online identities, a digital pen-pal romance, and one party finding out before the other but continuing the ruse anyway. We could be talking about Sierra Burgess Is a Loser, or we could be talking about the Meg Ryan/Tom Hanks rom-com You've Got Mail. Much like the characters in Sierra Burgess, indie bookstore owner Kathleen and corporate bookseller Joe develop a close relationship online, without realizing that they're professional rivals in real life. Once Joe realizes who his pen pal "Shopgirl" is, he continues the deception but doesn't anticipate how their feelings will both develop.