Film
28 voters

The Best Movies About Dating In High School

Updated August 28, 2020 663 votes 28 voters36 items

List RulesVote up your favorite movies where high school students start dating.

Which of these films are the best movie about dating in High school? That's what we are here to determine with the help of your votes. High school is a time of contradictions. It's both magical and excruciating, both exciting and exhausting, and nowhere is it more confusing than in the world of dating and relationships.

These dating in high school films range from relatively realistic films like The Fault In Our Stars, to musical romps, like Grease. They show all sides of dating in high school. The unspoken crushes, the tempestuous romances, the bullies, and the broken hearts.

Teenage romcoms like these are a relatively new genre. They got their start with the films of John Hughes in the 80s, films like Pretty In Pink, Sixteen Candles and The Breakfast Club. Since then, the genre has exploded, with the popular teen movies of the 90s like 10 Things I Hate About You, which helped launch the career of Heath Ledger. While the genre never really went away, it's recently experienced a resurgence, thanks to movies like Netflix's To All The Boys I've Loved Before.

So whether you're in high school right now or you're looking to relive those times, take a look at this list of the best dating in high school movies. Vote for your favorites, and add anything we might have missed.

  • 1
    23
    4

    The Fault in Our Stars

    Shailene Woodley, Willem Dafoe

    Released2014

    Directed byJosh Boone

    The Fault in Our Stars is a 2014 American romantic drama film directed by Josh Boone, based on the novel of the same name by John Green. The film stars Shailene Woodley, Ansel Elgort, and Nat Wolff,...  more
  • 2
    24
    8

    To All the Boys I've Loved Before

    Lana Condor, Janel Parrish

    Released2018

    Directed bySusan Johnson

    To All the Boys I've Loved Before is a 2018 American teen romance film directed by Susan Johnson, based on the 2014 novel by Jenny Han. Lara Jean Song Covey (Lana Condor) writes private love letters...  more
  • 3
    18
    2

    Clueless

    Alicia Silverstone, Brittany Murphy

    Released1995

    Directed byAmy Heckerling

    Clueless is a 1995 American comedy film loosely based on Jane Austen's 1815 novel Emma. It stars Alicia Silverstone, Stacey Dash, Paul Rudd, and Brittany Murphy. The film is set in Beverly Hills and...  more
  • 4
    21
    8

    Sixteen Candles

    John Cusack, Molly Ringwald

    Released1984

    Directed byJohn Hughes

    Sixteen Candles is a 1984 American coming-of-age comedy film starring Molly Ringwald, Michael Schoeffling and Anthony Michael Hall. It was written and directed by John Hughes....  more
  • 5
    11
    2

    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

    Released1999

    Directed byGil Junger

    10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and a modern retelling of William Shakespeare's The Taming of the Shrew. After finding out his crush (Larisa...  more
  • 6
    13
    5

    American Pie

    Alyson Hannigan, Tara Reid

    Released1999

    Directed byChris Weitz, Paul Weitz

    American Pie is a 1999 teen comedy film written by Adam Herz and directed by brothers Paul and Chris Weitz, in their directorial film debut. It is the first film in the American Pie theatrical...  more
  • 7
    12
    4

    The Kissing Booth

    Joey King, Joel Courtney

    Released2018

    Directed byVince Marcello

    The Kissing Booth is a 2018 romantic comedy film directed by Vince Marcello. A pretty, teenage girl (Joey King), who has never-been-kissed, finds her life turned totally upside down when she decides...  more
  • 8
    13
    6

    High School Musical

    Vanessa Hudgens, Ashley Tisdale

    Released2006

    Directed byKenny Ortega

    High School Musical is a 2006 American teen/children's romantic comedy musical television film and the first installment in the High School Musical trilogy. Upon its release on January 20, 2006, it...  more
  • 9
    16
    10

    Grease

    John Travolta, Olivia Newton-John

    Released1978

    Directed byRandal Kleiser

    Grease is a 1978 American musical romantic comedy-drama film directed by Randal Kleiser and produced by Paramount Pictures. It is based on Warren Casey and Jim Jacobs' 1971 musical of the same name...  more
  • 10
    13
    8

    Say Anything...

    John Cusack, Jeremy Piven

    Released1989

    Directed byCameron Crowe

    Say Anything... is a 1989 American romantic comedy-drama film written and directed by Cameron Crowe in his directorial debut. In 2002, Entertainment Weekly ranked Say Anything... as the greatest...  more
  • 11
    7
    2

    17 Again

    Zac Efron, Michelle Trachtenberg

    Released2009

    Directed byBurr Steers

    17 Again is a 2009 American comedy film directed by Burr Steers. The film follows 37-year-old Mike who becomes a 17-year-old high school student after a chance incident. The film also features Leslie...  more
  • 12
    13
    10

    Easy A

    Emma Stone, Amanda Bynes

    Released2010

    Directed byWill Gluck

    Easy A is a 2010 American teen comedy film directed by Will Gluck. A clean-cut high school student (Emma Stone) relies on the school's rumor mill to advance her social and financial standing....  more
  • 13
    10
    8

    John Tucker Must Die

    Jenny McCarthy, Sophia Bush

    Released2006

    Directed byBetty Thomas

    This film is a 2006 American high school comedy romance film, directed by Betty Thomas. The film is about a trio of girls who plot to break the heart of manipulative basketball star John Tucker after...  more
  • 14
    13
    13

    Can't Hardly Wait

    Jennifer Love Hewitt, Melissa Joan Hart

    Released1998

    Directed byDeborah Kaplan, Harry Elfont

    Can't Hardly Wait is a 1998 American teen comedy film written and directed by Deborah Kaplan and Harry Elfont. It stars an ensemble cast including Jennifer Love Hewitt, Ethan Embry, Charlie Korsmo,...  more
  • 15
    13
    13

    Fast Times at Ridgemont High

    Nicolas Cage, Sean Penn

    Released1982

    Directed byAmy Heckerling

    Fast Times at Ridgemont High is a 1982 American coming-of-age teen comedy film written by Cameron Crowe, adapted from his 1981 book of the same name. As a freelance writer for Rolling Stone magazine,...  more
  • 16
    13
    13

    Never Been Kissed

    Jessica Alba, Drew Barrymore

    Released1999

    Directed byRaja Gosnell

    Never Been Kissed is a 1999 romantic comedy film produced by 20th Century Fox and Drew Barrymore's production company, Flower Films, directed by Raja Gosnell and starring Drew Barrymore, David...  more
  • 17
    9
    8

    The Perks of Being a Wallflower

    Emma Watson, Nina Dobrev

    Released2012

    Directed byStephen Chbosky

    The Perks of Being a Wallflower is a 2012 American coming-of-age comedy-drama film, and an adaptation of the 1999 epistolary novel of the same name; it was written and directed by the novel's author,...  more
  • 18
    5
    0

    To All the Boys: P.S. I Still Love You

    Ross Butler, Noah Centineo

    Released2020

    Directed byMichael Fimognari

    To All the Boys: P.S. I Still Love You is a 2020 American teen romantic comedy film directed by Michael Fimognari, based on Jenny Han's 2015 novel P.S. I Still Love You and a sequel to the 2018 film...  more
  • 19
    8
    6

    High School Musical 2

    Zac Efron, Vanessa Hudgens

    Released2007

    Directed byKenny Ortega

    High School Musical 2 is an American musical film directed by Kenny Ortega. High school student Troy Bolton (Zac Efron) stresses over getting a job, with the price of college expenses looming on his...  more
  • 20
    5
    0

    The Kissing Booth 2

    Joey King, Molly Ringwald

    Released2020

    Directed byVince Marcello

    The Kissing Booth 2 is a 2020 American teen romantic comedy film directed by Vince Marcello....  more
  • 21
    10
    10

    Love Don't Cost a Thing

    Nicole Scherzinger, Christina Milian

    Released2003

    Directed byTroy Bailey

    Love Don't Cost a Thing, stylized as Love Don't Co$t a Thing, is a 2003 teen comedy film written and directed by Troy Beyer and starring Nick Cannon and Christina Milian It also stars Steve Harvey,...  more
  • 22
    10
    10

    Pretty in Pink

    James Spader, Gina Gershon

    Released1986

    Directed byHoward Deutch

    Pretty in Pink is a 1986 American romantic comedy-drama film about love and social cliques in 1980s American high schools. It is one of John Hughes' films starring Molly Ringwald, and is commonly...  more
  • 23
    1
    0

    Chemical Hearts

    Lili Reinhart, Austin Abrams

    Released2020

    Directed byRichard Tanne

    Chemical Hearts is a 2020 American romantic drama film directed by Richard Tanne, based on the novel Our Chemical Hearts by Krystal Sutherland. Teenage student, Henry Page (Austin Abrams), considers...  more
  • 24
    8
    7

    High School Musical 3: Senior Year

    Vanessa Hudgens, Ashley Tisdale

    Released2008

    Directed byKenny Ortega

    High School Musical 3: Senior Year is a 2008 American teen romantic comedy musical film and the third installment in the High School Musical series. Produced and released on October 24, 2008 by Walt...  more
  • 25
    1
    1

    The Half of It

    Leah Lewis, Alexxis Lemire

    Released2020

    Directed byAlice Wu

    The Half of It is a 2020 American coming-of-age dramedy, written and directed by Alice Wu. Shy, straight-A student Ellie Chiu (Leah Lewis) feels isolated and friendless in her remote, backwater town...  more