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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.
| Name | Character | Team | |
|---|---|---|---|
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Amber Paul | Jill | Unowned |
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Donna Lynne Champlin | Gena | Unowned |
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Kiera Allen | The Young Woman | Unowned |
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David Arrow | Hank | Unowned |
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Elijah Guo | The Young Man | Unowned |
| Andrew Arrow | Ben | Unowned | |
| Tom Alan Robbins | The Man | Unowned | |
| Eliza Simone Bradley | The Girl | Unowned | |
| Candice Clarke | Funeral Director | Unowned | |
| Charles Arrow | Boy in park | Unowned | |
| Arsenio Stembridge | Bar patron | Unowned | |
| Stewart Clarke | Mourner | Unowned | |
| William English | Mourner | Unowned | |
| Anne Ferguson | Mourner | Unowned | |
| Christine Kohler | Mourner | Unowned | |
| Aaron Netsky | Mourner | Unowned |