There’s something about one’s first love that is so special. For many people this occurs during one’s teenage years, when bodies are changing and hormones are pumping. Everything is new and intense. While most of these affairs are fleeting, they can lay the foundation for relationships to come and give one someone to stalk on Instagram at 2am in the later years of their life, wondering what could have been.
The ten movies on this list explore the ups, downs, and painfully beautiful moments of teenage romance. Watch them to experience it all over again, preferably with a face mask on to prevent pesky zits from popping up.
To All The Boys I’ve Loved Before
As you’re growing up, it is a pretty normal occurrence to get crushes on people you interact with. In this Netflix film, Lara Jean, played by Lana Condor, experiences this and because of her introverted nature decides to express herself by writing each of her five crushes a letter she never intends to send. When her sister Kitty sends them, chaos ensues because one of Lara Jean’s crushes is her older sister’s ex-boyfriend. The great news about this film is if you love it there is so much more for you to watch, including two other films and a future Netflix series XO, Kitty. You can also read the book series of the same name by Jenny Han.
Love and Basketball
Sometimes love is closer than you think. When Monica Wright, played by Sanaa Lathan, moves next door to Quincy McCall, played by Omar Epps, they discover they have more in common than geography, sharing a deep love for basketball. It will take them much longer to discover they also love each other as their mutual desire to pursue careers as professional athletes gets in the way of their on and off again relationship. This movie was written by and marked Gina Prince-Bythewood’s feature directorial debut. Watch it on HBO Max to see if Monica and Quincy can have it all.
Love, Simon
It is never easy to be different from the perceived norm, but this is amplified by a thousand when one is a teenager. Simon Spier, played by Nick Robinson, knows this all too well as he is hiding his sexuality from most of the world except a new penpal named Blue. Unfortunately, another student, Martin, finds out Simon’s secret and uses it against him. Can Simon accept and love himself so he can find love offline? You are going to have to watch this film on Hulu to find out. If you love the movie, read the source material Simon vs. the Homo Sapiens Agenda by Becky Albertalli.
Easy A
The rumor mill of high school can be devastatingly difficult to navigate. Olive Penderghast, played by Emma Stone, tries to use it to her advantage but quickly loses control. In order to get out of a camping trip with her friend Rhiannon Abernathy, played by Aly Michalka, Olive lies and says she lost her virginity to a college boy. Word quickly spreads and soon Olive finds herself lying and saying she slept with many boys at school to help their reputations. While the gift card compensation she receives is fun at first, high school gossip can be cruel and these arrangements cannot last. To see how Olive gets herself out of this jam and if she can find her own love story, watch this movie on Peacock. As a bonus, this film also boasts an incredible cast including Stanley Tucci, Patricia Clarkson, Thomas Haden Church, Amanda Bynes, Penn Badgley, and Lisa Kudrow.
Crush
Sometimes when you finally get what you think you wanted, you realize you didn’t really want it and find something unexpectedly better. This is the case in this 2022 film, Crush. Paige Evans, played by Rowan Blanchard, wants nothing more than to get into CalArts and to get close to her crush Gabby. She joins the track team to accomplish both only to make a surprising discovery. Rounding out the cast is Megan Mullally playing Angie Evans who is Paige’s mother. You can stream this film on Hulu.
The Fault in Our Stars
This 2014 film was based on a 2012 John Green novel of the same name. Its plot centers on two teenagers who meet through a cancer support group, Hazel Grace Lancaster, played by Shailene Woodley, and Augustus “Gus” Waters, played by Ansel Elgort. They bond over their mutual love of literature and soon embark on their own literary adventure in Amsterdam. Teenage love is fleeting enough but when cancer diagnoses are added to the mix, things become even more complicated. To see how Hazel and Gus navigate these heavy issues of love, life, and death, watch this movie currently available on HBO Max.
Clueless
Any romantic movie list without some Jane Austen representation would be severely lacking. Thankfully this 1995 film loosely based on Jane Austen’s novel Emma legitimizes this list. Clueless updates the classic novel and places it in Beverly Hills, California. Cher Horowitz, played by Alicia Silverstone, finds she enjoys setting up people and believes she has a knack for it. She soon learns that meddling in people’s love lives comes at a cost. To find out how Cher comes to this realization while trying to give the new girl at school a makeover, watch this movie on Paramount Plus. As a bonus, the cast also includes Stacey Dash, Brittany Murphy and Paul Rudd.
10 Things I Hate About You
This classic teenage romance film is based on another classic, William Shakespeare’s The Taming of the Shrew. New student Cameron James, played by Joseph Gordon-Levitt, is immediately smitten with the popular Bianca Stratford, played by Larisa Oleynik. The only issue is Bianca is not allowed to date until her older sister Kat, played by Julia Stiles, does, and Kat is, well… difficult. Cameron becomes part of a scheme to get Kat dating and hijinks ensue. This film is a treasure trove of popular ’90s stars including the late Heath Ledger, Andrew Keegan, and Gabrielle Union. It also contains deep quotes such as: “I know you can be overwhelmed, and you can be underwhelmed, but can you ever just be whelmed?” To find out how “whelmed” you are by this film, watch it on Disney+.
The Perks of Being a Wallflower
Sometimes teens just want to blend in and disappear. This is the case for depressed teen Charlie Kelmeckis, played by Logan Lerman, as he begins his freshman year, but instead he soon makes friends with seniors Sam, played by Emma Watson, and Charlie, played by Ezra Miller. His English teacher Mr. Anderson, played by Paul Rudd, offers his sage advice as Charlie makes his way through his freshman year and navigates not only high school but his mental health challenges. This film is a rare instance of being as good as the source material it is based on, in part because it was written and directed by Stephen Chbosky who also wrote the novel. To accept the love you deserve, watch this film on Hulu.
Everything, Everything
Teens always think their parents are overprotective, but in Maddy Whittier’s case this is very much true. Maddy, played by Amandla Stenberg, has an immune disorder and is not allowed to leave the house. This does not prevent her from falling for the boy next door, Oliver “Olly” Bright, played by Nick Robinson. As the lovebirds grow closer, new truths about Maddy’s health condition come to light. Rent this film on Amazon to see what Maddy’s mother has been hiding from her.