The best romance films set in high school utilize social cues and adolescent feelings to provide obstacles for their main characters. The pressure to fit in with others, the insecure feelings associated with unrequited love, and social cliques that seem impossible to diffuse are all foundational concepts for teen romance films. No matter one's age, such emotions and circumstances can be understood by a wide range of audiences, which helps these films remain relevant and pleasant to watch decades later.
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10 Secret Admirer (1985)
Anonymous Love Letters Are Sent Back And Forth
David Greenwalt, who'd eventually become best known for his work on Buffy the Vampire Slayer and Angel, directed Secret Admirer at the height of the sex comedy genre in the mid-80s. Secret Admirer starts with a simple plot: before entering his senior year of high school, Michael Ryan (C. Thomas Howell) receives an anonymous love letter he assumes is from his crush, Deborah (Kelly Preston). In reality, the letter was penned by his friend Toni Williams (Lori Loughlin), who harbors a secret crush on Michael.
Despite its predictability, Secret Admirer is consistently funny all the way through, and the characters are slightly more nuanced than those typically included in a teen rom-com. Unlike most high school romance films, a significant portion of Secret Admirer is dedicated to the parental characters, but they're used wisely and don't take away from the central story involving the teens. Their storyline involves misguided assumptions about their spouses that culminate in a humorously over-the-top brawl during a bridge party.
9 Just One Of The Guys (1985)
An '80s Adaptation Of Shakespeare's Twelfth Night
Just One of the Guys is one of the earliest examples of a teen comedy film adapted from William Shakespeare's work. Twelfth Night acts loosely as the inspiration for Just One of the Guys' premise, which sees a struggling teenage journalist, Terri Griffith (Joyce Hyser), transfer to a rival school in hopes of getting a better response to her articles. At the new school, Terri modifies her name to "Terry" and enrolls as a boy.
Like She's the Man, another popular teen comedy adaptation of Twelfth Night, the joy of Just One of the Guys comes from seeing Terri navigate interactions with other students, especially those she develops romantic feelings towards. The film's premise is entertaining on its own, but it only truly works if the leading actor is convincing in their role, and, thankfully, Hyser is. Hyser takes command of the film with her comedic timing and charm and comes off as a likable protagonist audiences want to see succeed.
8 Can't Buy Me Love (1987)
A Deal Is Made Between A School's Nerd And Cheerleader
The consensus among critics states that Can't Buy Me Love would have worked better if its commentary on the desire to be popular was amped up and further explored. However, the film still works well as a teen comedy with an obvious but important message. Can't Buy Me Love follows Ronald Miller (Patrick Dempsey), an unnoticed high school student who makes a deal with popular cheerleader Cindy Mancini (Amanda Peterson). The deal is that Cindy will pretend to be Ronald's girlfriend for a month, and Ronald will pay for an expensive outfit Cindy destroyed.
However, Ronald quickly learns that being popular is not all that it's cracked up to be. With the rise of social media and the ability to gain instant virality, the message of Can't Buy Me Love has become increasingly more relevant. Dempsey is compelling as the astronomy-obsessed nerd turned off-putting popular jerk and is paired nicely with Peterson, who proves there is more to her cheerleading character that could have easily been one-dimensional.
7 Valley Girl (1983)
Teenagers From Different Worlds Fall In Love
Minus the feuding families and tragic ending, Valley Girl bears a slight resemblance to William Shakespeare's Romeo and Juliet. The opposing young lovers at the center of Valley Girl are the popular Julie (Deborah Foreman) and city punk Randy (Nicolas Cage). Despite their mutual attraction towards one another, the two are surrounded by people who advise them not to be together. Just like other Romeo and Juliet-inspired films, Valley Girl explores the dilemma that comes with wanting to adhere to others' expectations, whilst also yearning for a life outside of one's social bubble.
Because of its inspiration from Shakespeare's work, the story of Valley Girl is predictable but is kept fresh with a comedic script, a solid new wave soundtrack, and strong performances. It is easy for valley girl characters in movies to be portrayed without depth, but Foreman's performance prevents this from being the case, and Cage's on-screen charisma makes it perfectly clear how Julie could fall for a guy like Randy.
6 Some Kind Of Wonderful (1987)
An Effective Reworked Version Of Pretty In Pink
Following their previous collaboration on Pretty in Pink, Howard Deutch and John Hughes collaborated once more for Some Kind of Wonderful, which they made in response to the former film's ending. The film has a similar premise, following outcast Keith Nelson (Eric Stoltz) as he pursues popular student Amanda Jones (Lea Thompson). Meanwhile, while helping out Keith, his best friend Watts (Mary Stuart Masterson) realizes she has feelings for him.
The gender-flipped aspect of Some Kind of Wonderful, with Stoltz acting in place of Molly Ringwald's character, works well, and the script has some uniquely comedic moments that land. While Some Kind of Wonderful would have greatly benefited from a narrative that wasn't as similar to Pretty in Pink, the film still has its shining moments that warrant frequent revisiting. The lead actors, Stoltz, Thompson, and Masterson, are lively in their roles and encapsulate what Hughes has become known for — writing tangible characters, specifically teens, trying to find their way in the world.
5 Sixteen Candles (1984)
A Mediocre Birthday Is Made Worse By An Unrequited Crush
John Hughes' directorial debut, Sixteen Candles, was a massively influential film that changed Hollywood's perception of teenage stories on the big screen. Sixteen Candles stars Molly Ringwald as Sam Baker, a 16-year-old with a crush on a senior classmate, Jake Ryan (Michael Schoeffling). Watching Sixteen Candles years later is fascinating, as it kickstarted a whole trend of films being centered around teenage life, which has grown to be a massively popular genre of film today. Still, Sixteen Candles is not without unpleasant "of its time" aspects.
There are unavoidable harsh realities about Sixteen Candles that dampen the experience of a rewatch. Yet, the film's legacy has endured all these years because of the aforementioned influence on Hollywood, in addition to its memorable leading performances. Ringwald, Schoeffling, and Anthony Michael Hall portray their teenage characters as easily identifiable figures audiences can relate to, separating Hughes' film from others. Sixteen Candles was refreshing at the time of its release because Hughes' script felt like a more accurate representation of '80s teenagers in the way they spoke and viewed life.
4 Gregory's Girl (1980)
A Soccer Player Falls For The New Girl On His Team
From the UK, Gregory's Girl is a beloved coming-of-age romance story that can be enjoyed by audiences worldwide. The film centers around the titular teenager, played by John Gordon Sinclair, getting replaced in his position on the school's soccer team by a classmate, Dorothy (Dee Hepburn). Dorothy's beauty and athletic skills impress Gregory, and he works up the courage to ask her out on a date. Gregory's Girl isn't full of clichés typically included in films about teenage romance.
Instead, the film is a bit quieter and highlights the awkward parts of young love and growing up. Sinclair plays Gregory's awkwardness in a way that audiences are likely to relate to, rather than outright cringe at, and he's supported by a range of actors that make up the film's comical characters. Gregory's Girl captures the graceless moments of adolescence with a sweet and nostalgic approach that often makes the film more enjoyable years later.
3 Say Anything... (1989)
A High School Graduate Falls For An Unlikely Girl
Cameron Crowe, who had a hand in many memorable '80s and '90s films like Fast Times at Ridgemont High and Jerry Maguire, made his directorial debut with Say Anything..., starring John Cusack and Ione Skye. Unlike other high school romance films mentioned, Say Anything... takes place right after its high school students have graduated, with the underachieving but optimistic Lloyd Dobler (Cusack) working up the courage to ask out the valedictorian, Diane Court (Skye). However, their love story is not without complications, as Diane's father does not approve of Lloyd.
Say Anything..., partially because it takes place after graduation, puts its characters through a more mature struggle compared to other teen romance movies at the time. The characters are transitioning into adulthood and gradually come to take control of their lives, deciding who they want to be (and be with). Both Skye and Cusack deliver endearing performances, with the latter's desperate and determined boombox gesture being the scene largely associated with the film years later.
2 Pretty In Pink (1986)
Starring Brat Pack members Molly Ringwald and Andrew McCarthy, Pretty in Pink brings a standard romance story to life with a witty script and memorable performances. Pretty in Pink follows teenager Andie Walsh (Ringwald) as she's preparing to attend her senior prom with a rich, popular boy, Blane McDonnagh (McCarthy). Like most movies set in high school, Pretty in Pink lays out the opposing social cliques throughout school, which results in bullying incidents and feelings of insecurity audiences can connect with.
However, an added aspect of class division among the student body adds a bit more depth to the film and makes it easier to watch decades later. Because of their differing positions within the high school social setting, certain expectations are put on Andie and Blane, both by audiences and characters within the film. Since its release, Pretty in Pink has continued to be a beloved film, and that's partially because of its soundtrack. Like many Brat Pack films, Pretty in Pink's soundtrack was filled with new wave music, representing the genre's rise in popularity within the United States.
1 Peggy Sue Got Married (1986)
Transported To Her Past, A Girl Reevaluates Her Love Life
Francis Ford Coppola's The Outsiders was a hit at the box office, but the films that came after would prove to be less successful with audiences — until Peggy Sue Got Married in 1986. The love story in Coppola's fantasy comedy film captivated audiences. Differing from the decade's other high school romance movies, Peggy Sue Got Married begins by introducing its characters as adults attending their high school reunion. When the titular character (played by Kathleen Turner) is crowned the reunion's queen, she passes out and wakes up during her senior year of high school.
Peggy Sue Got Married isn't groundbreaking in the romance genre, but it does entertain mature themes about love, regret, and living in the moment, which is part of why it still holds up so well years later. The biggest gripe critics had about Peggy Sue Got Married was the performance by Nicolas Cage, who plays Peggy's recently divorced husband she married out of high school. Still, Peggy Sue Got Married is one of Coppola's best films and is a delightful, nostalgic watch.
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