1. The Graduate (1967)
Coming-of-age often means sexual awakening, and that’s what happens when Benjamin (Dustin Hoffman) gets seduced by Mrs. Robinson (Anne Bancroft). But The Graduate is also about Benjamin figuring out what he wants to do with his life (not plastics) — and ultimately who he wants to be with. And then perhaps realizing what you thought you wanted isn’t what you wanted after all.
2. Harold and Maude (1971)
Cross-generational romance has never been handled better than in Harold and Maude, in which Harold (Bud Cort) comes of age through his relationship with much older wild child Maude (Ruth Gordon). Of course, the film deals not only with Harold’s first love but also — spoiler alert — his first real experience of death, as Maude chooses to end her life at 80.
3. Sixteen Candles (1984)
John Hughes made some of the most iconic coming-of-age romances of all time, and Sixteen Candles is one of the finest. As Sam (Molly Ringwald) turns 16, she’s predictably obsessed with sex and boys — particularly hunky senior Jake Ryan (MIchael Schoeffling). There are moments that feel dated, but the film as a whole captures the awkward phase well.
4. Pretty in Pink (1986)
Then there’s Pretty in Pink, another John Hughes film starring Molly Ringwald. Again, it’s about finding one’s place in high school, but the romance here is more complicated, as Andie (Ringwald) has to deal with her crush on rich kid Blane (Andrew McCarthy) and attention from her best friend Duckie (Jon Cryer), who’s in love with her.
5. Dirty Dancing (1987)
Baby (Jennifer Grey) is a sheltered rich girl vacationing with her family at a resort in the Catskills. She soon falls for dance instructor Johnny (Patrick Swayze), who is far more mature. (After all, he’s into dirty dancing.) In order to come into her own, Baby has to break free from her overbearing family. Remember, nobody puts Baby in a corner.
6. Say Anything… (1989)
Everyone remembers Say Anything… for the scene where John Cusack holds a boombox over his head, but there’s more to it than that. It takes place the summer after high school — a popular setting for the coming-of-age romance — as Lloyd Dobler (Cusack) tries to win over valedictorian Diane Court (Ione Skye), who is moving to England at the end of the summer.
7. My Girl (1991)
Vada (Anna Chlumsky) grows up fast in My Girl: She’s lost her mother and is dealing with a distant father and feelings for her best friend Thomas J. (Macaulay Culkin). Their love story is short-lived and tragic — Thomas J. gets stung by hornets and dies from his allergy. And suddenly children all over learned how depressing romance can be.
8. Now and Then (1995)
Now and Then distinguishes itself as a coming-of-age film because it shows the main characters as girls and as adults. They deal with family problems, questions of identity, and first love in the ’70s — and then we see how they turned out as adults. It answers a question often overlooked by coming-of-age movies: What happens after those formative teenage years?
9. The Incredibly True Adventure of Two Girls in Love (1995)
Loner teenager Randy (Laurel Holloman) is stuck in a hopeless pursuit of a married woman named Wendy (Maggie Moore). But things look up when she meets Evie (Nicole Ari Parker), a girl from the right side of the tracks. As in other ’90s LGBT romances, the film focuses on both young women coming to terms with their identities.
10. Casper (1995)
While not a traditional romance, Casper does deal with the experience of growing up and discovering love — even if the object of one’s affections is long dead. Kat (Christina Ricci) and Casper (Devon Sawa) have a chaste romance, but their slow dance at the end is proof that, under other circumstances, they could have been more than friends.
11. Beautiful Thing (1996)
When it comes to LGBT romance, Europe has always been ahead of the game. Beautiful Thing tells the story of high school students Jamie (Glen Berry) and Ste (Scott Neal). The film is set in Thamesmead, a working class area of London, emphasizing the added difficulty of finding oneself and growing up in a restrictive conservative environment.
12. Romeo + Juliet (1996)
There are plenty of adaptations of Romeo and Juliet to choose from, but Baz Luhrmann’s is the best fit for the coming-of-age romance genre. By casting two major teen stars of the time — Leonard DiCaprio and Claire Danes — he made Shakespeare’s love story more relatable to a new generation of high school students, all too familiar with impossible love.
13. Edge of Seventeen (1998)
The year is 1984. The place is Sandusky, Ohio. And Eric (Chris Stafford) struggles with his sexuality while finding himself drawn to openly gay college student Rod (Andersen Gabrych). While the simple plot may sound trite now, Edge of Seventeen was one of the first major coming-of-age gay romances, and it set the stage for many of the films that followed.
14. Rushmore (1998)
Of course Max (Jason Schwartzman) is never going to make it work with elementary school teacher Rosemary (Olivia Williams), but that doesn’t make Rushmore any less poignant. Besides, unrequited love is an essential part of every young person’s development. With its style, Rushmore became especially influential to a certain group of people — I won’t call them hipsters.
15. Can’t Hardly Wait (1998)
It’s not always easy to leave high school behind: For Preston (Ethan Embry), that means confessing his four-year crush on prom queen Amanda (Jennifer Love Hewitt). The title Can’t Hardly Wait and the film’s setting, a high school graduation party, reflect the overwhelming desire to grow up fast and move past the awkwardness of adolescence.
16. But I’m a Cheerleader (1999)
Megan (Natasha Lyonne) doesn’t understand why her parents shipped her off to conversion camp to “cure” her lesbianism. Once there, however, she realizes she’s gay after all when she discovers feelings for Graham (Clea DuVall). While most LGBT films in this genre are about coming out to family, this is more about coming out to oneself.
17. Step Up (2006)
Yes, a dance movie can also be a coming-of-age romance. (See also: Dirty Dancing.) It’s about dancing, yes, but also about growing up and the relationship between Tyler (Channing Tatum) and Nora (Jenna Dewan). (She’s now Jenna Dewan Tatum, so you know how that real-life love story turned out.) And yes, Channing Tatum has sweet moves.
18. ATL (2006)
T.I. makes his acting debut as Rashad in ATL. His life isn’t easy, as he’s forced to balance work and high school, and a budding relationship with New-New (Lauren London), a girl who may be a bad influence. Rashad’s coming-of-age is complicated by his difficult circumstances and New-New lying about her identity, which makes his perseverance all the more impressive.
19. Charlie Bartlett (2007)
Numbed by prescription drugs and dealing with a depressed mother, Charlie Bartlett (Anton Yelchin) is having a hard time growing up. Part of his maturation comes from dispensing therapy and pills to his classmates, but it’s also his relationship with Susan (Kat Dennings), who happens to be the principal’s daughter. Always pragmatic, Charlie learns to develop emotionally.
20. Juno (2007)
Juno is less about the love story between Juno (Ellen Page) and Paulie (Michael Cera) than it is about Juno growing up through a very adult experience — getting pregnant and having a baby. As she matures, though, we see her opting for an age-appropriate romance: She’s grown up enough to realize cool older man Mark (Jason Bateman) isn’t right for her.
21. Let the Right One In (2008)
Only one vampire romance belongs on this list, and no, it’s not Twilight. Bullied 12-year-old Oskar (Kåre Hedebrant) bonds with his mysterious neighbor Eli (Lina Leandersson). In many ways their love story is innocent, even as Eli literally kills for Oskar, because Oskar is too young to fully understand his feelings — not to mention what Eli truly is.
22. Nick and Norah’s Infinite Playlist (2008)
That Nick (Michael Cera) and Norah (Kat Dennings) will fall in love is a foregone conclusion. What’s interesting is the way this coming-of-age romance takes place a little after they’ve both come of age: As it turns out, there’s more growing up to do. In particular, the film involves a sexual awakening, as both characters discover the importance of a woman’s sexual pleasure.
23. Adventureland (2009)
James (Jesse Eisenberg) is excited to go off to grad school until he finds out he has to pay for it himself. He takes a summer job at Adventureland amusement park, where he meets the stunning (and unavailable) Emily (Kristen Stewart). The 1987 setting adds nostalgia to a story about falling in love with the wrong person and trying to make it work anyway.
24. The Perks of Being a Wallflower (2012)
High school freshman Charlie (Logan Lerman) is having a hard time adjusting until he meets fellow outcasts Sam (Emma Watson) and Patrick (Ezra Miller). As he slowly comes out of his shell, he grows more and more attracted to Sam, even as he dates another girl. The movie is based on the book of the same name, which inspired an endless amount of adolescent angst when it was released in 1999.
25. Moonrise Kingdom (2012)
The kids in Moonrise Kingdom are — well, just that. But even kids fall in love, or at least get the kind of adolescent crush that feels an awful lot like the real thing. It’s less a movie about growing up and more about trying to rush to adulthood, as the young couple runs away to start a new life with one another, free from the bonds of society (and parents).