Dynamic Watchlist Hub: May 15, 2026

10 Best Movies Like Dear Roy, Love Gillian

If you loved Dear Roy, Love Gillian, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for Dear Roy, Love Gillian.

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#1
The United States of Leland

The United States of Leland

2003★ 6.5

Why watch this? A perfect follow-up to Dear Roy, Love Gillian for fans of Crime. It captures a similar emotionally gripping atmosphere.

A withdrawn young man, Leland Fitzgerald is imprisoned for the murder of a mentally disabled boy, who also happened to be the brother of his girlfriend, Becky.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 str...

#2
After

After

2019★ 7.1

Why watch this? A perfect follow-up to Dear Roy, Love Gillian for fans of Drama. It captures a similar emotionally gripping atmosphere.

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...

#3
Fire with Fire

Fire with Fire

1986★ 6.2

Why watch this? A perfect follow-up to Dear Roy, Love Gillian for fans of Drama. It captures a similar emotionally gripping atmosphere.

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, ...

#4
In the Good Old Summertime

In the Good Old Summertime

1949★ 6.7

Why watch this? A perfect follow-up to Dear Roy, Love Gillian for fans of Comedy. It captures a similar light-hearted atmosphere.

Two co-workers in a music shop dislike one another during business hours but unwittingly carry on an anonymous romance through the mail....

#5
Endless Love

Endless Love

2014★ 6.9

Why watch this? A perfect follow-up to Dear Roy, Love Gillian for fans of Drama. It captures a similar emotionally gripping atmosphere.

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

The Mustang

2019★ 6.9

Why watch this? A perfect follow-up to Dear Roy, Love Gillian for fans of Drama. It captures a similar emotionally gripping atmosphere.

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 hi...

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