10 Movies Like Clueless | Beautiful Teenage Love Stories!


Teenage romances and high school love stories are evergreen magic that can stir hearts always as we correlate our old days. Thanks to the cinema, there are many beautiful teenage stories like Clueless (1995) that have drama, romance, and a lot of fun. Well, there are many movies like Clueless that have similar charm and intensity.

Amy Heckerling’s Clueless was released on 19 July 1995. The decades-old love drama flick is still fresh and appealing. The characters and plot of the movie highlight the intensity of peer pressure, complicated love stories, and dramatic events. The movie boasts 6.9/10 IMDb and 81% Rotten Tomatoes scores. There are some more popular movies like Clueless that are worth watching.

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10 Movies Like Clueless | Beautiful Teenage Love Stories!

Clueless is considered one of the most iconic movies and for all the right reasons. The movie is full of high-voltage comedy-drama from top-notch stories to interesting characters. The movie’s protagonist, Cher, is an enthusiastic self-proclaimed matchmaker and a messiah in her surrounding. However, soon her life gets complicated due to her obsession with helping people! 

The movie has epic dialogues, a complicated teenage love story, and a lot of drama that will make you roll out on the floor. Well, keeping this movie in mind, here are some more evergreen, juicy, and entertaining comedy-dramas, inspiring, and romantic movies like Clueless to make your day! Check out the complete list below.

Also, Read | 8 Movies Like Five Feet Apart | Love Stories That Will Make You Cry!

#1 Love, Simon (2018)

10 Movies Like Clueless | Beautiful Teenage Love Stories!

Love, Simon is a beautiful story of a teenager named Simon who happens to be gay! He struggles hard to keep his secrets from his family and friends, but things go out of his hands when he starts dating a boy in his class. Simon continuously hides his true identity until an unknown person starts blackmailing him. 

Thus, Simon gets trapped and is forced to take drastic steps that forever change his life. Just like Clueless, this movie also focuses on high-school issues and complexities. Thus making it one of the entertaining movies like Clueless on our list.

Release Date: 27 February 2018 

Genre:  Romance/Drama

Director: Greg Berlanti 

Movie Run Time: 1h 50m

Cast: Nick Robinson, Jennifer Garner, Josh Duhamel, Katherine Langford, Keiynan Lonsdale, Alexandra Shipp, and Logan Miller

IMDB Score: 7.6/10

Rotten Tomatoes Score: 92%

Where You Can Watch: Disney+

#2 Emma (2020)

10 Movies Like Clueless | Beautiful Teenage Love Stories!

Similar to the Clueless plot, Emma also shares similar characters and vibes. The movie’s protagonist, Emma, tries to help her friends. Every time she crosses her limits, things get out of control. Her advice leads to more breakups and complicated love lives rather than solving the issues. 

However, her misadventures lead her to find her own Prince Charming in the most unexpected ways. Thus, the story has many layers of emotions in a comic tone that is amusing. Thus, Emma is one of the beautiful movies like Clueless that you cannot skip out on watching.  

Release Date: 13 February 2020   

Genre: Romance/Drama 

Director: Autumn de Wilde

Movie Run Time: 2h 4m

Cast: Anya Taylor-Joy, Johnny Flynn, Mia Goth, Angus Imrie, Letty Thomas, Gemma Whelan, and Bill Nighy

IMDB Score: 6.7/10 

Rotten Tomatoes Score: 86%

Where You Can Watch: Prime Video

#3 The DUFF (2015)

10 Movies Like Clueless | Beautiful Teenage Love Stories!

The DUFF is one of my favorites flick that I never get bored of watching. If you haven’t heard of this awesome flick, here is a luring plot at your service! The movie is a funny high-school drama that subtly highlights sensitive issues like body-shaming and bullying. The protagonist, Bianca, realizes that her classmates and friends only use her for their greedy purposes. 

Moreover, she discovers that she is named DUFF, aka Designated Ugly Fat Friend. A disheartened but self-determined Bianca decides to bounce back. She takes the help of her best friend in return for teaching him science. Moreover, she decides to cut off all the toxic people for her good. Thus, the DUFF is one of the most inspiring movies like Clueless on this list. 

Release Date: 20 February 2015  

Genre: Comedy/Teen 

Director: Ari Sandel

Movie Run Time:  1h 41m

Cast:  Mae Whitman, Bella Thorne, Robbie Amell, Allison Janney, Skyler Samuels, Bianca A. Santos, and Romany Malco 

IMDB Score: 6.5/10

Rotten Tomatoes Score: 73%

Where You Can Watch: Prime Video

Also, Read | 8 Enchanting Movies Like Me Before You | Life-Changing Flicks!

#4 10 Things I Hate About You (1999)

10 Movies Like Clueless | Beautiful Teenage Love Stories!

10 Things I Hate About You has everything you will love to watch! The movie has a hilarious plot of a misadventure teenage love story and many sweet yet funny conspiracies. The plot revolves around Bianca and her boyfriend Cameron, who want to officially date each other. However, Bianca can not do this because her elder sister, Kat, hates dating. 

Thus, the duo hires a mysterious guy to impress and charm Kat. However, things take hilarious twists and turns that are fun to watch. 10 Things I Hate About You is surely one of the best entertaining movies like Clueless that you won’t regret watching.

Release Date: 31 March 1999  

Genre: Romance/Comedy

Director: Gil Junger

Movie Run Time: 1h 37m

Cast: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik, Susan May Pratt, Andrew Keegan, and David Krumholtz  

IMDB Score: 7.3/10

Rotten Tomatoes Score: 70%

Where You Can Watch: Disney+

#5 Legally Blonde (2001)

10 Movies Like Clueless | Beautiful Teenage Love Stories!

Another masterpiece on this list is Legally Blonde. The movie boasts of a hilarious yet inspiring teenage love story and high-school drama. The movie’s protagonist, Ella, enrolls herself in her ex-boyfriend’s school to seek him back. However, she comes across many struggles and discovers her self-worth instead. 

This sweet revenge story has many funny moments that will give you a good laugh. Like Clueless, this movie also comically centers around love and relationships. Thus, Legally Blonde is one of the most entertaining movies like Clueless that you should not miss out on watching this summer!  

Release Date: 5 October 2001   

Genre: Comedy/Romance

Director: Robert Luketic

Movie Run Time: 1h 36m

Cast: Reese Witherspoon, Luke Wilson, Selma Blair, Matthew Davis, Victor Garber, Jennifer Coolidge, and Holland Taylor

IMDB Score: 6.4/10

Rotten Tomatoes Score: 70% 

Where You Can Watch: Prime Video

#6 Mean Girls (2004)

10 Movies Like Clueless | Beautiful Teenage Love Stories!

Mean Girls movie needs no introduction as it is already proclaimed an iconic movie by our generation! The movie has spicy dialogues, intriguing characters, and stellar performers that are enough to trigger our senses. The movie revolves around a teenager named Cady, admitted to high school. However, Regina’s bully group makes her life hell. 

Thus, Cady bounces back with her friends- Janis and Damian, to teach them a lesson. Moreover, during her revenge, she turns herself into a very different personality that no one has expected! The movie is a fun riot due to its epic punchlines and funny content. 

Release Date: 3 September 2004 

Genre: Comedy/Teen

Director: Mark Waters

Movie Run Time:  1h 37m

Cast: Lindsay Lohan, Jonathan Bennett, Rachel McAdams, Tina Fey, Lacey Chabert, Ana Gasteyer, Lizzy Caplan, Tim Meadows, and Amy Poehler

IMDB Score: 7.1/10

Rotten Tomatoes Score: 84%

Where You Can Watch: Netflix 

#7 Never Been Kissed (1999)    

10 Movies Like Clueless | Beautiful Teenage Love Stories!

Never Been Kissed is another awesome movie like Clueless that will take you back to the old lanes of high school memories. The movie is a dramatic romance rather than a light-hearted comedy. The story revolves around a passionate journalist named Josie, who joins high school as an undercover student. 

She meets many people there who change her life forever. Moreover, she bumps into her past secrets that freshen her old pains. Well, Josie finds an escape from her miseries and fights back her odds bravely. 

Release Date: 9 April 1999 

Genre: Romance/Comedy

Director: Raja Gosnell

Movie Run Time: 1h 47m

Cast: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon, John C. Reilly, Garry Marshall, Sean Whalen, and Cress Williams

IMDB Score: 6/10

Rotten Tomatoes Score: 55% 

Where You Can Watch:  Disney+ 

Also, Read | 10 Romantic Movies Like After We Collided | Love Stories You Will Fall In Love With   

#8 Easy A (2010)

10 Movies Like Clueless | Beautiful Teenage Love Stories!

Easy A is a hilarious high school drama that will give you a good laugh. The movie portrays high school enthusiasm, related complications, and peer pressure in a very funny way. The protagonist, Olive, tries to act cool and spreads a very weird rumor about herself- She is no more a virgin! 

However, things backfire drastically as her classmates start to make fun of her and bully her for having a bad character. Thus, a frustrated Olive decides to solve all the mess and sets a mission to reveal the truth. However, there are many obstacles ahead that she needs to face first. Thus, her hilarious misadventure is fun to watch on a monotonous day.


Release Date: 12 November 2010 

Genre: Comedy/Romance

Director: Will Gluck 

Movie Run Time: 1h 32m

Cast: Emma Stone, Amanda Bynes, Penn Badgley, Dan Byrd, Thomas Haden Church, Patricia Clarkson, and Cam Gigandet

IMDB Score:  7/10

Rotten Tomatoes Score: 85%

Where You Can Watch: Netflix

#9 Cruel Intentions (1999)

10 Movies Like Clueless | Beautiful Teenage Love Stories!

The Cruel Intention is more like a seductive tale rather than a rom-com. However, just like Clueless, the movie focuses on different layers of emotions and fairytale love stories. The story revolves around two step-siblings, Sebastian and Kathryn, who are notoriously stubborn and can go to any length to win their bets. 

However, things take a sharp u-turn when Kathryn challenges Sebastian to charm Annette and sleep with her. In return, she promises that she will accept his proposal. Well, Sebastian gets successful, but he falls in love with Annette for real. But things get weird when the truth comes out. Thus, this high-voltage erotic drama is worth watching.

Release Date: 5 March 1999  

Genre: Romance/Drama

Director: Roger Kumble

Movie Run Time: 1h 37m

Cast: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Joshua Jackson, Selma Blair, Louise Fletcher, and Eric Mabius 

IMDB Score: 6.8/10

Rotten Tomatoes Score: 54%

Where You Can Watch: Prime Video

#10 Booksmart (2019)

10 Movies Like Clueless | Beautiful Teenage Love Stories!

Last but not least, Booksmart is an awesome flick similar to Clueless in terms of fun and drama that you should not miss out on watching. The story is about two highly studious girls named Molly and Amy, who finally take a break from studies to explore outside life. 

However, their adventurous journey leads them to hilarious troubles that complicate their smooth-going lives. The movie has many funny moments and insightful thoughts to keep your spirits high. 

Release Date: 10 March 2019

Genre: Comedy/Teen

Director: Olivia Wilde

Movie Run Time: 1h 42m

Cast: Kaitlyn Dever, Beanie Feldstein, Jessica Williams, Jason Sudeikis, Victoria Ruesga, Lisa Kudrow, and Will Forte 

IMDB Score: 7.1/10

Rotten Tomatoes Score:  96%

Where You Can Watch: Netflix

Also, Read | 9 Infatuating Movies Like The Kissing Booth | A Deep Dive Into The Pool Of Teen Rom-Coms!

Final Words

The Clueless movie is a beautiful rom-com that has high standards of entertainment. However, the movies mentioned above like Clueless are not less in anything either! So, do not miss out on watching these popularly entertaining movies. If you have already enjoyed them all, tell us about your favorite flick that entertained you the most in the comment section.

Sabira Fatimi
Sabira Fatimi
Sabira, The magical fresh air of the Viebly, can bewitch you through her awesome writings on our site! A daydreamer, wordsmith, charmer, camera-poser, and hodophile are her other personalities to explore. She is a writer who never fails to fascinate with her brilliant storytelling; after all, she is the postgraduate historian of Jamia! She is the chatter-box of the team who never fails to raise unending queries and keep everyone amused. She is the Khaleesi of her imaginary realm riding her ferocious dragons as a free-spirit. I had told you….She is that dramatic!


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