Film

The Best Movies About Dating In High School 

Ranker Film
Updated February 12, 2020 302 votes 24 voters 33 items

List Rules Vote 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.

list ordered by
1
Clueless is listed (or ranked) 1 on the list The Best Movies About Dating In High School
Alicia Silverstone, Brittany Murphy, Paul Rudd

Released: 1995

Directed by: Amy 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 ...more
2
10 Things I Hate About Y... is listed (or ranked) 2 on the list The Best Movies About Dating In High School
Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger

Released: 1999

Directed by: Gil Junger

10 Things I Hate About You is a 1999 American teen romantic comedy-drama film. It is directed by Gil Junger and stars Julia Stiles, Heath Ledger and Joseph Gordon-Levitt. The romantic comedy ...more
3
The Fault in Our Stars ... is listed (or ranked) 3 on the list The Best Movies About Dating In High School
Shailene Woodley, Willem Dafoe, Laura Dern

Released: 2014

Directed by: Josh 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 ...more
4
Easy A is listed (or ranked) 4 on the list The Best Movies About Dating In High School
Emma Stone, Amanda Bynes, Aly Michalka

Released: 2010

Directed by: Will Gluck

Easy A is a 2010 film directed by Will Gluck. "After a little white lie about losing her virginity gets out, a clean-cut high school girl (Emma Stone) sees her life paralleling Hester ...more
5
Sixteen Candles is listed (or ranked) 5 on the list The Best Movies About Dating In High School
John Cusack, Molly Ringwald, Joan Cusack

Released: 1984

Directed by: John 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.
6
To All the Boys I've Lov... is listed (or ranked) 6 on the list The Best Movies About Dating In High School
Lana Condor, Janel Parrish, Anna Cathcart

Released: 2018

Directed by: Susan 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 ...more
7
17 Again is listed (or ranked) 7 on the list The Best Movies About Dating In High School
Zac Efron, Michelle Trachtenberg, Matthew Perry

Released: 2009

Directed by: Burr 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 ...more
8
John Tucker Must Die is listed (or ranked) 8 on the list The Best Movies About Dating In High School
Jenny McCarthy, Sophia Bush, Brittany Snow

Released: 2006

Directed by: Betty 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 ...more
9
The Perks of Being a Wal... is listed (or ranked) 9 on the list The Best Movies About Dating In High School
Emma Watson, Nina Dobrev, Paul Rudd

Released: 2012

Directed by: Stephen 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 ...more
10
Bring It On is listed (or ranked) 10 on the list The Best Movies About Dating In High School
Kirsten Dunst, Eliza Dushku, Gabrielle Union

Released: 2000

Directed by: Peyton Reed

Bring It On is a 2000 American teen comedy film that was directed by Peyton Reed and written by Jessica Bendinger. It was followed by four direct-to-video sequels, none of which contain any of ...more
11
Say Anything... is listed (or ranked) 11 on the list The Best Movies About Dating In High School
John Cusack, Jeremy Piven, Joan Cusack

Released: 1989

Directed by: Cameron 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
12
Mean Girls is listed (or ranked) 12 on the list The Best Movies About Dating In High School
Lindsay Lohan, Rachel McAdams, Amanda Seyfried

Released: 2004

Directed by: Mark Waters

Mean Girls is a 2004 American teen comedy film. Mark Waters directed, and Tina Fey wrote the screenplay, which is based in part on Rosalind Wiseman's non-fiction book Queen Bees and Wannabes, ...more
13
American Pie is listed (or ranked) 13 on the list The Best Movies About Dating In High School
Alyson Hannigan, Tara Reid, Shannon Elizabeth

Released: 1999

Directed by: Chris 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
14
High School Musical is listed (or ranked) 14 on the list The Best Movies About Dating In High School
Vanessa Hudgens, Ashley Tisdale, Zac Efron

Released: 2006

Directed by: Kenny 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, ...more
15
The Kissing Booth is listed (or ranked) 15 on the list The Best Movies About Dating In High School
Joey King, Joel Courtney, Jacob Elordi

Released: 2018

Directed by: Vince 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 ...more
16
Can't Hardly Wait is listed (or ranked) 16 on the list The Best Movies About Dating In High School
Jennifer Love Hewitt, Melissa Joan Hart, Jaime Pressly

Released: 1998

Directed by: Deborah 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 ...more
17
Fast Times at Ridgemont ... is listed (or ranked) 17 on the list The Best Movies About Dating In High School
Nicolas Cage, Sean Penn, Jennifer Jason Leigh

Released: 1982

Directed by: Amy 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 ...more
18
Never Been Kissed is listed (or ranked) 18 on the list The Best Movies About Dating In High School
Jessica Alba, Drew Barrymore, James Franco

Released: 1999

Directed by: Raja 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
19
Ranker Video
Ross Butler, Noah Centineo, Lana Condor

Released: 2020

Directed by: Michael 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 ...more
20
Love Don't Cost a Thing ... is listed (or ranked) 20 on the list The Best Movies About Dating In High School
Nicole Scherzinger, Christina Milian, Nick Cannon

Released: 2003

Directed by: Troy 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 ...more
21
Pretty in Pink is listed (or ranked) 21 on the list The Best Movies About Dating In High School
James Spader, Gina Gershon, Molly Ringwald

Released: 1986

Directed by: Howard 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 ...more
22
Grease is listed (or ranked) 22 on the list The Best Movies About Dating In High School
John Travolta, Olivia Newton-John, Stockard Channing

Released: 1978

Directed by: Randal 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 ...more
23
She's All That is listed (or ranked) 23 on the list The Best Movies About Dating In High School
Sarah Michelle Gellar, Anna Paquin, Lil' Kim

Released: 1999

Directed by: Robert Iscove

She's All That is a 1999 American teen romantic comedy film directed by Robert Iscove and starring Freddie Prinze, Jr. and Rachael Leigh Cook. It is a modern adaptation of George Bernard Shaw's ...more
24
Better Off Dead is listed (or ranked) 24 on the list The Best Movies About Dating In High School
John Cusack, E.G. Daily, David Ogden Stiers

Released: 1985

Directed by: Savage Steve Holland

This film is a 1985 American teen romantic comedy film starring John Cusack and written and directed by Savage Steve Holland. It tells the story of high school student Lane Myer after his ...more
25
High School Musical 2 is listed (or ranked) 25 on the list The Best Movies About Dating In High School
Zac Efron, Vanessa Hudgens, Ashley Tisdale

Released: 2007

Directed by: Kenny 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 ...more