Movies Like Dear Roy, Love Gillian

If you liked Dear Roy, Love Gillian (1992), a movie directed by Graham Theakston, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
The United States of Leland (2003)
★ 6.5/10
A withdrawn young man, Leland Fitzgerald is imprisoned for the murder of a mentally disabled boy, who also happened to be the brother of his girlfriend, Becky. As the community struggles to deal with the killing, Pearl…
2
Fire with Fire (1986)
★ 6.2/10
A tough, street-smart kid serving a sentence in a state youth reformatory meets a beautiful, innocent girl studying at a nearby convent. When forbidden love blossoms between them, they must fight the prison…
3
In the Good Old Summertime (1949)
★ 6.8/10
Two co-workers in a music shop dislike one another during business hours but unwittingly carry on an anonymous romance through the mail.
4
Paper Towns (2015)
★ 6.2/10
Quentin Jacobsen has spent a lifetime loving the magnificently adventurous Margo Roth Spiegelman from afar. So when she cracks open a window and climbs back into his life dressed like a ninja and summoning him for an…
5
Endless Love (2014)
★ 6.9/10
A privileged girl and a charismatic boy's instant desire sparks a love affair made only more reckless by parents trying to keep them apart.
6
The Mustang (2019)
★ 6.9/10
While participating in a rehabilitation program training wild mustangs, a convict at first struggles to connect with the horses and his fellow inmates, but he learns to confront his violent past as he soothes an…
7
Mary and Max (2009)
★ 7.9/10
A tale of friendship between two unlikely pen pals: Mary, a lonely, eight-year-old girl living in the suburbs of Melbourne, and Max, a forty-four-year old, severely obese man living in New York.
8
Blue Story (2019)
★ 7.3/10
Blue Story is a tragic tale of a friendship between Timmy and Marco, two young boys from opposing postcodes. Timmy, a shy, smart, naive and timid young boy from Deptford, goes to school in Peckham where he strikes up a…
9
Banana Split (2018)
★ 6.6/10
After a messy breakup with her high school boyfriend, April strikes up an unexpected platonic friendship with his new girlfriend, Clara.
10
Love, Rosie (2014)
★ 7.8/10
Since the moment they met at age 5, Rosie and Alex have been best friends, facing the highs and lows of growing up side by side. A fleeting shared moment, one missed opportunity, and the decisions that follow send…
11
After (2019)
★ 7.1/10
Tessa Young is a dedicated student, dutiful daughter and loyal girlfriend to her high school sweetheart. Entering her first semester of college, Tessa's guarded world opens up when she meets Hardin Scott, a mysterious…
12
Heathers (1989)
★ 7.2/10
A girl who halfheartedly tries to be part of the "in crowd" of her school meets a rebel who teaches her a more devious way to play social politics: by killing the popular kids.
13
Mr. Right (2016)
★ 6.4/10
A girl falls for the "perfect" guy, who happens to have a very fatal flaw: he's a hitman on the run from the crime cartels who employ him.
14
The Unforgivable (2021)
★ 7.4/10
A woman is released from prison after serving a sentence for a violent crime and re-enters a society that refuses to forgive her past.
15
Keith (2008)
★ 7/10
Natalie is high school royalty, but her queen bee status falls apart when she falls for the new guy at school. Although Keith ignores her at first, they soon become friends -- even though Natalie suspects that Keith…
16
The Best of Me (2014)
★ 7.5/10
A pair of former high school sweethearts reunite after many years when they return to visit their small hometown.
17
The Other Zoey (2023)
★ 7/10
Highly intelligent computer major Zoey Miller is uninterested in romantic love, but her life is turned upside down when Zack, the school's soccer star, gets amnesia and mistakes Zoey for his girlfriend.
18
Secret Admirer (1985)
★ 6.7/10
An anonymous love letter left in Michael Ryan's locker on the last day of school wreaks havoc on his life and the lives of everyone who comes in contact with it.
19
D.E.B.S. (2005)
★ 6.6/10
The star of a team of teenage crime fighters falls for the alluring villainess she must bring to justice.
20
Enola Holmes (2020)
★ 7.2/10
While searching for her missing mother, intrepid teen Enola Holmes uses her sleuthing skills to outsmart big brother Sherlock and help a runaway lord.