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The Best Movies About Dating In High School

Updated August 28, 2020 659 votes 26 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
    The Fault in Our Stars is listed (or ranked) 1 on the list The Best Movies About Dating In High School
    21
    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... more on Wikipedia
  • 2
    To All the Boys I've Loved Bef is listed (or ranked) 2 on the list The Best Movies About Dating In High School
    23
    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... more on Wikipedia
  • 3
    Clueless is listed (or ranked) 3 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 4
    Sixteen Candles is listed (or ranked) 4 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 5
    10 Things I Hate About You is listed (or ranked) 5 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 6
    American Pie is listed (or ranked) 6 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 7
    The Kissing Booth is listed (or ranked) 7 on the list The Best Movies About Dating In High School
    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...
  • 8
    High School Musical is listed (or ranked) 8 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 9
    Grease is listed (or ranked) 9 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 10
    Say Anything... is listed (or ranked) 10 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 11
    17 Again is listed (or ranked) 11 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 12
    Easy A is listed (or ranked) 12 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 13
    John Tucker Must Die is listed (or ranked) 13 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 14
    Can't Hardly Wait is listed (or ranked) 14 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 15
    Fast Times at Ridgemont High is listed (or ranked) 15 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 16
    Never Been Kissed is listed (or ranked) 16 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 17
    The Perks of Being a Wallflowe is listed (or ranked) 17 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 18
    To All the Boys: P.S. I Still  is listed (or ranked) 18 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 19
    High School Musical 2 is listed (or ranked) 19 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 20
    The Kissing Booth 2 is listed (or ranked) 20 on the list The Best Movies About Dating In High School
    4
    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.
  • 21
    Love Don't Cost a Thing is listed (or ranked) 21 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 22
    Pretty in Pink is listed (or ranked) 22 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 23
    Chemical Hearts is listed (or ranked) 23 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 24
    High School Musical 3: Senior  is listed (or ranked) 24 on the list The Best Movies About Dating In High School
    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... more on Wikipedia
  • 25
    The Half of It is listed (or ranked) 25 on the list The Best Movies About Dating In High School
    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.... more on Wikipedia
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