Mr. D - Season 5 - Eps 13: Gerry Turns 40
Gerry is turning forty, and after finding a letter he wrote to himself ten years earlier, he becomes acutely aware of everything he has failed to accomplish. Meanwhile, Simon's ferret goes missing and Lisa wants to impress the chairman of the board of trustees by putting on an elaborate fun fair in his honour, which quickly devolves into a complete disaster.
About Mr. D

Title: Mr. D
First Air Date: 2012-01-09
Last Air Date: 2018-12-19
Status: Ended
Rating: 7.423/10 (from 26 votes)
Language: EN
Seasons: 8
Total Episodes: 88
Network: CBC Television
Genres: Comedy
Production Companies: Topsail Entertainment
Synopsis
Based on Gerry Dee's real-life experiences as a high school teacher before he switched to comedy full-time, MR. D is a story about a charming, under-qualified teacher trying to fake his way through a teaching job, just like he often fakes his way through life.
Cast

Jonathan Torrens
Robert Cheeley

Booth Savage
Principal Callaghan

Gerry Dee
Mr. D

Lauren Hammersley
Lisa Mason

Bette MacDonald
Trudy Walsh