In Five Questions, Jill, played by Amber Paul, comes to terms with an early trauma in her life. In each of the film's five scenes, a question is asked that propels Jill forward and toward an answer that opens a path to resolution.
| Actor | Role |
|---|---|
 Amber PaulJill | Jill |
 Donna Lynne ChamplinGena | Gena |
 Kiera AllenThe Young Woman | The Young Woman |
 David ArrowHank | Hank |
 Elijah GuoThe Young Man | The Young Man |
| AAndrew ArrowBen | Ben |
| TTom Alan RobbinsThe Man | The Man |
| EEliza Simone BradleyThe Girl | The Girl |
| CCandice ClarkeFuneral Director | Funeral Director |
| CCharles ArrowBoy in park | Boy in park |
| AArsenio StembridgeBar patron | Bar patron |
| SStewart ClarkeMourner | Mourner |
| WWilliam EnglishMourner | Mourner |
| AAnne FergusonMourner | Mourner |
| CChristine KohlerMourner | Mourner |
| AAaron NetskyMourner | Mourner |