Dear Leo follows the story of Annie Duncan as she graduates from high school and starts her freshman year of college, as told through the perspective of letters with her middle-school cousin Leo.
| Actor | Role |
|---|---|
| JJill YoungAnnie Duncan | Annie Duncan |
| CCaroline BeaglesScottie Kay | Scottie Kay |
| AAlexandra IntratorHayden Lopez | Hayden Lopez |
| LLauren WeikMolly Harbin | Molly Harbin |
 Fazia RizviLisa Duncan | Lisa Duncan |
| AAustin HilleConnor Green | Connor Green |
| EEthan BernardiniLeo Bennett | Leo Bennett |
| SSanjay VattamreddyJared C. | Jared C. |
| FFinley PfardrescherJared M. | Jared M. |
| PPaul GrubbCarl Duncan | Carl Duncan |
| MMaren AlfordSamantha T. | Samantha T. |
| WWill ClarkJosh Sutherland | Josh Sutherland |
 Alex AlfordClint the Tour Guide | Clint the Tour Guide |