Bob created his Lil' Cutie several years prior, garnering some success with it. It is rumored that his comic strip is based off of his son when he was a child. Greg Heffley speculates that he has begun to have trouble coming up with new material as his son is fully grown.
Bob decides to retire and stop making Lil' Cutie, slating the final strip for August. However, the strip is continued when Tyler decides to take over from his father.
- Due to the fact that his son is 32 years old, he must be at least 50, although is most likely in his 60s.