Jeffrey has been nominated for several awards including Outstanding Director - Play at the Drama Desk Awards for Christopher Ashley, Outstanding New Play at the Drama Desk Awards for Paul Rudnick, Direction at the Obie Awards for Christopher Ashley, Performance at the Obie Awards for Edward Hibbert, and Playwriting at the Obie Awards for Paul Rudnick. Additionally, Jeffrey has received nominations for Best Off Broadway Play and the John Gassner Playwriting Award at the Outer Critics Circle Awards, both of which were awarded to Paul Rudnick.