10 Funny & Romantic Flicks Similar to ’10 Things I Hate About You’

In this modernized version of William Shakespeare’s classic comedy The Taming of the Shrew, 10 Things I Hate About You follows the life of the keep-to-herself teenager Kat Stratford. Though smart and pretty, she is not as well regarded among the high school, having pushed many away with her cynical behavior and antisocial approach. Her disinterest with her peers only further aggravates her younger sister Bianca for the very specific household rule that requires both siblings must have boyfriends or none of them will. Angered, Bianca seeks to fix this by setting Kat up with a date, tapping the latest bad boy in town, Patrick Verona, to fit the bill. But what starts as an arranged dating situation may turn into true romance. It’s a quirky romantic comedy that comes from director Gil Junger (Black Knight) and writers Karen McCullah (Legally Blonde) and Kirsten Smith (Ella Enchanted), with an astounding cast of talented youngsters that includes Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt.

Though taking its cues from Shakespeare, 10 Things I Hate About You fit neatly into the genre of teen rom-coms where love can be found in the most unexpected of places. The good news is that anyone who seeks a marathon of similar teen comedies, be they works ripped from Shakespeare or not, were plentiful amid the era. Here are ten more films to consider that match the coming-of-age quirks present in 10 Things I Hate About You.

Fast Times at Ridgemont High

Teenager Stacy Hamilton may appear to be one of the most beautiful girls in school but the truth is she is inexperienced when it comes to matters of love. Seeking to get into a relationship, she seeks out the advice of her peers to find the right guy. But what starts out as finding one guy soon turns into her being entwined in a love triangle between the nice guy Mark Ratner and the bad boy Mike Damone. Meanwhile, the stoner Jeff Spicoli finds himself coasting through high school while easily angering his short-fused teacher Mr. Hand. Directed by Amy Heckerling (National Lampoon’s European Vacation), written by Cameron Crowe (Almost Famous), this coming-of-age teen comedy features an ensemble cast that includes Sean Penn, Jennifer Jason Leigh, Judge Reinhold, Phoebe Cates, Brian Backer, Robert Romanus, and Ray Walston.

Never Been Kissed

Josie Geller is a fresh-faced copywriter who is seeking some research on the high school scene by posing as a student. Returning to her old high school to study the ways of teenagers has made her realize how much things have changed. Her investigation also runs into trouble when her secrecy is threatened by Josie falling for one of the teachers, making her question how far she’s willing to go undercover or throw it all away for love. Directed by Raja Gosnell (Big Momma’s House) and written by Abby Kohn (He’s Just Not That Into You) and Marc Silverstein (Valentine’s Day), this romantic comedy of recapturing high school youth stars Drew Barrymore, David Arquette, Michael Vartan, Leelee Sobieski, Jeremy Jordan, Molly Shannon, Garry Marshall, and John C. Reilly.

Can’t Hardly Wait

The high school seniors of Huntington Hillside have finally arrived at graduation day, ready to leave behind high school forever. To celebrate such a milestone, a collective of the students gather for a house party. All sorts of social circles come for the party, ranging from popular girls to the roughest of jocks to the nerdiest of nerds. Among them is the artsy Preston who is hoping that this party will be his chance to confess his love to his long-time crush of Amanda. Also present at the party is the geeky William who uses this event as the perfect opportunity to get his revenge on the bully Mike. And the rapping Kenny finds himself in an unorthodox situation at the party when trapped in a room with the cynical Denise. Written and directed by Deborah Kaplan and Harry Elfont  (Josie and the Pussycats), this one-wild-night teen comedy features an ensemble cast of Ethan Embry, Charlie Korsmo, Lauren Ambrose, Peter Facinelli, Seth Green, and Jennifer Love Hewitt.

American Pie

As high school comes to an end, a group of teenage boys find that they haven’t really lived the teenage lifestyle to the fullest. Namely, they haven’t had sex. Seeking to change this fact, they form a pact to lose their virginity before the high school year is finished. Thus begins a desperate and hilarious race to see who can have sex the first in this raunchy teen comedy that results in one of the boys engaging in relations with a warm apple pie. Directed by Paul Weitz (Down to Earth, About a Boy) and written by Adam Herz (Go Fish), this hit of a teen sex comedy features a comedic assortment of actors that includes Jason Biggs, Chris Klein, Natasha Lyonne, Thomas Ian Nicholas, Seann William Scott, Tara Reid, Mena Suvari, and Eugene Levy. The film was not only enough of a success to warrant the sequels of American Pie 2 (2001), American Wedding (2003), and American Reunion (2012) but the film also branched off into a spin-off franchise with numerous direct-to-video films in the series.


Jane Austen’s classic novel of Emma gets a 1990s makeover in this modern teen comedy. Cher Horowitz is a teen who resides in the upscale life of being a high school student living in Beverly Hills. As a beautiful and rich girl, she decides to use her knowledge of fashion and makeup to help out the new girl in school become more socially acceptable. But Char may discover there’s more to life than just the best clothes or the best look. Written and directed by Amy Heckerling (Fast Times at Ridgemont High), this cult teen comedy of the 1990s starred Alicia Silverstone, Stacey Dash, Brittany Murphy, Paul Rudd, and Wallace Shawn. The film’s success led to a short-lived sitcom spin-off as well as a remake to be developed by Paramount.

Mean Girls

Based on the novel Queen Bees and Wannabes by Rosalind Wiseman, Mean Girls takes place in the harsh world of the high school social scene. Having not been in school much since venturing off to Africa with her parents, Cady Heron is surprised by how rigid American schools can be when it comes to social interaction. She is soon filled with how the school’s social order works and is inducted into the clique of The Plastics, one of the most popular groups in the school. However, when further examining how the school functions, she realizes that such a hierarchy cannot stand. Her new mission becomes to dismantle such social norms that are begging to be torn down. Directed by Mark Waters (Head over Heels) and written by Tina Fey (Baby Mama), the sleeper hit of a teen comedy stars Lindsay Lohan, Rachel McAdams, Tim Meadows, Ana Gasteyer, Amy Poehler, and Tina Fey.


James is a recent college grad who is finding life outside of school a tough world to navigate when it comes to finding work. The best job he can muster is a summer gig at the local Adventureland theme park, helping out with rides and carnival games. Thankfully, he’s not the only aimless young adult who finds little thrill in working at such a place, spending is off hours partying, drinking and smoking weed with an eclectic group of new friends. There may even be romance in the air, though he may not be ready for the love triangle he has just entered into with the lovely Em. Written and directed by Greg Mottola as his next film after Superbad, this sleeper teen dramedy stars Jesse Eisenberg, Kristen Stewart, Martin Starr, Bill Hader, Kristen Wiig, Margarita Levieva, Ryan Reynolds.

Jennifer’s Body

Jennifer was considered the hottest girl in high school but now may have the new title of the deadliest girl in school. When she becomes possessed by the spirit of a demon, her body starts to crave human flesh, leading to Jennifer seeking and eating teenage boys. But her carnage can only go on for so long when her nerdy friend Needy learns the truth and sets out to stop Jennifer’s rampage of blood and gore. Directed by Karyn Kusama (The Invitation) and written by Diablo Cody (Juno), this off-beat teen horror stars Megan Fox, Amanda Seyfried, Johnny Simmons, J. K. Simmons, Amy Sedaris, and Adam Brody.

Better Off Dead

Lane Meyer is a teenager who finds himself severely down in the dumps. He has just broken up with his girlfriend Beth and is finding himself so bitterly depressed he tries to commit suicide. But when he meets a foreign exchange student, he becomes inspired to rise up to not only change his mind on suicide but beat the snooty jock in a challenge of skiing down one of the toughest mountains in the area. Written and directed by Savage Steve Holland (One Crazy Summer), this ridiculous 1980s comedy features a cast that includes John Cusack, Curtis Armstrong, Diane Franklin, David Ogden Stiers, and Kim Darby.

Lady Bird

Christine McPherson is nearly finished with school and seeking to get more out of her adult and college years. Doing so, however, finds her lying to both her friends and family to achieve the life she so strives to attain, be it the college of her choice of the boy she fancies most. But life isn’t so easy and she often finds herself struggling to get along with others, struggling to rise above her poor parents but not resort to the scummy levels of the upper class snobs in school. Written and directed by Greta Gerwig (Little Women), this touching coming-of-age dramedy was nominated for five Academy Awards (including Best Picture) and features emotional performances by the likes of Saoirse Ronan, Laurie Metcalf, Tracy Letts, Lucas Hedges, and Timothée Chalamet.

Leave a Reply

Your email address will not be published.