Set in the shadow of the 2009 Madoff scandal, Bill is a recently retired, rural Ontario English teacher, struggling to move on from the loss of his wife two years prior. The play explores themes of grief, loss and the challenge of change later in life. Encouraged by his friend Ben, who has ulterior motives, Bill reluctantly wades into the dating scene. It soon becomes apparent that Bill is quite unprepared for this new life, as he interacts with a series of strong female characters. Of course it all goes horribly wrong for Bill and Ben, to great comedic effect.
Keywords: Aging, grief, dating, grammar, comedy
Production history:
Staged reading performance by Markham Little Theatre, February 2026
Genre: Comedy
Acts: 2
Run time: 120 minutes
Suitable for students 14+
Cast size: 9 actors
Male roles: 3
Female roles: 6
Casting notes: This play was written for amateur theatre groups, with lots of parts for older women.
