screenshot of High School Musical

High School Rom-Coms You’ll Fall Head Over Heels For

Looking for a love story to keep you occupied during the pandemic? Try these five romantic comedies.
November 21, 2020
9 mins read

With the pandemic keeping everyone holed-up in their homes, now is the perfect time to curl up in bed and revisit some nostalgic high school love stories. Listed below are some of the best teenage romantic comedies, including both recent releases and early 2000s throwbacks. Although each movie centers around a high school romance, the themes vary, ranging from the heartbreak of cancer to the joy of singing basketball players. Each one of the films will either have you laughing hysterically or bawling uncontrollably, so get prepared for a rollercoaster of emotions as you embark on this movie marathon.

5. “She’s the Man” (2006)

When the funding for her high school girls soccer team is cut, Viola (Amanda Bynes) dons a wig and pretends to be her twin brother, Sebastian, in order to join his boarding school soccer team. Her plan starts off smoothly, but complications arise when Viola falls for her brother’s dreamboat of a roommate, Duke (Channing Tatum).

Duke, unfortunately, only has eyes for his classmate Olivia (Laura Ramsey), but Olivia doesn’t reciprocate his feelings, especially once she realizes how cute Duke’s new roommate, “Sebastian,” is. Soon, Viola’s situation becomes so convoluted that getting out of it with her dignity would take a miracle. What will go down when the truth finally comes out?

Based on Shakespeare’s “Twelfth Night,” this wacky comedy combines all the fun of high school relationships with the intrigue of dress-up and twin switcheroos. Those looking for a film grounded in realism may not be satisfied by this movie, but if you’re willing to suspend your disbelief, you’ll get a kick out of the wacky storyline and over-the-top acting. Bynes steals the show with her quirky, tomboyish character, contributing to the film’s countless number of laugh-out-loud moments.

4. Five Feet Apart (2019)

Cystic fibrosis patients Stella (Haley Lu Richardson) and Will (Cole Sprouse) meet in a hospital at the start of Will’s B. cepacia drug trial. Although the two appear to be polar opposites — Stella is a picture-perfect patient who struggles with OCD, while Will’s persona oozes danger and angst — their initial personality clash soon gives way to a romantic spark.

The only catch? Cystic fibrosis patients are not allowed within several feet of each other because of potential bacterial cross-infection. Dating is a nearly impossible task. With such a precarious situation, it’s only a matter of time before tragedy strikes.

This film will certainly bring you to tears, whether they be of joy or of sadness. Both Richardson and Sprouse put on a stunning performance. Their comedic energy is heartwarming, but more importantly, they bring raw emotion to the movie’s most heartbreaking scenes. “Five Feet Apart” also manages to spread awareness of cystic fibrosis without romanticizing the illness.

3. Love, Simon (2018)

As he puts it, Simon Speir (Nick Robinson) lives a “totally, perfectly normal life.” His only problem? He hasn’t told anyone that he’s gay. At the start of his senior year, Simon begins an anonymous email exchange with a mysterious boy at his school, “Blue.” But when Martin (Logan Miller), a socially-awkward drama geek, discovers Simon’s secret, Simon finds himself compromising his friendships to protect what he and Blue have. Will Simon be able to find his happy ending?

When “Love, Simon” debuted in 2018, it became an instant hit. The movie celebrates the LGBTQ+ community in a way that hasn’t been seen in many prior films. Although sexuality is a central theme, the movie is relatable to all teenagers; I find myself connecting with so many aspects of Simon’s story even though I don’t identify as LGBTQ+. “Love, Simon” has just the right amount of awkward, hilarious and cringe-worthy moments, but it still maintains the emotional depth needed to tell this type of story.

2. The Fault in Our Stars (2014)

Hazel Grace Lancaster (Shailene Woodley) is a 16-year old girl with thyroid cancer. At her cancer support group — which her mother forces her to attend — Hazel meets former osteosarcoma patient Augustus Waters (Ansel Elgort), who’s been in remission for 14 months.

Hazel and Gus quickly connect over their love for literature, their sarcasm and their “disdain for the conventional.” Despite the medical complications, the two eventually make plans to visit the author of Hazel’s favorite book, “An Imperial Affliction,” in Amsterdam, but the trip does not go exactly as planned, and it isn’t long before tragedy strikes.

Based on John Green’s novel “The Fault in Our Stars,” the film perfectly captures the book’s essence. Much of Hazel’s voice-over narration is taken directly from the novel’s pages, and the storyline is replicated to a tee.

Woodley and Elgort both bring their characters to life, capturing the sarcastic, unapologetic natures of Hazel and Gus. Supporting character Isaac (Nat Wolff), a close friend of the two leading characters and fellow cancer patient, also brings a wonderful sense of depth and passion to the story. When you watch this movie, make sure you have an adequate supply of Kleenex because “The Fault in Our Stars” is certain to leave you snot-nosed and teary-eyed.

1. High School Musical (2006)

Troy Bolton (Zac Efron) and Gabriella Montez (Vanessa Hudgens) meet singing karaoke at a New Year’s Eve party. Troy returns to school after winter break only to discover that Gabriella has transferred into his class at East High, home of the Wildcats. Even though the two teens have divergent interests — Troy is the captain of the basketball team, and Gabriella is, as she puts it, “the school’s freaky genius girl” — they end up auditioning for the school musical together on a whim.

The two must battle the interference of their friends, their other extracurriculars and the school’s mean girl, Sharpay Evans (Ashley Tisdale), in order to keep their musical pursuits and budding relationship intact.

Filled with drama, romance and wit, “High School Musical” is my go-to movie if I need a happiness boost. The storyline is entertaining, and the overall message about breaking free from stereotypes is important for high schoolers to hear.

The main reason this rom-com tops the rest is right there in the title — it’s a musical! Songs like “We’re All in This Together,” “Breaking Free” and “Start of Something New” have been on my personal playlist for years because of their catchy, upbeat melodies. And, of course, the dancing in “Get Your Head in the Game” and “Status Quo” has me jumping off the couch to join in every time. For those looking to supplement their “High School Musical” experience, make sure to check out the sequels as well.

Callie Rosenzweig, University of Chicago

Writer Profile

Callie Rosenzweig

University of Chicago

I’m Callie, a prospective psychology major originally from Palo Alto, CA. In my spare time I enjoy singing, watching sitcoms, hanging out with my stuffed animals and writing in my journal (aka my best friend).

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