A wildly inventive deconstruction of the romantic comedy built around the question: What would you do if you could travel to your loved ones’ past, heal their traumas, fix their problems, and change them into the perfect partner?
| Actor | Role |
|---|---|
 Kaley CuocoSheila | Sheila |
 Pete DavidsonGary | Gary |
 Deborah S. CraigJune | June |
 Sierra FiskSandra | Sandra |
 Wesley HollowayYoung Gary | Young Gary |
 Rock KohliAmit | Amit |
 Hari NefChai | Chai |
 Kevin CorriganPhil the Bartender | Phil the Bartender |
 Rebecca SchullGertrude | Gertrude |
 Pat BowieEthel | Ethel |
 Josy SorianoTatiana | Tatiana |
| AAndrew Stevens PurdyTeen Gary | Teen Gary |
| MMia MatysiakYoung Sheila | Young Sheila |
 Matthew WolfSoccer Announcer (voice) | Soccer Announcer (voice) |