New Year's Eve, the last hours of the year 1999. Kevin wants to lose his virginity, he had his chances before, but it just didn't happen. Will tonight be the night?
| Actor | Role |
|---|---|
 Steven YeunKevin | Kevin |
 Angela SprinkleChloe | Chloe |
 Max LesserJake | Jake |
| CColleen McGovernAmber | Amber |
| AAmanda TanguayBecky | Becky |
| JJoel WassermanSean Blackstone | Sean Blackstone |
| WWill CaseyRadio Host (voice) | Radio Host (voice) |