Jeff Dunham has become known as something of a family-friendly comedian. He may let the occasional, mild curse word slip out, but for the most part, people would consider him to be someone who “works clean.” Despite his multiple roles as a family man on shows like Home Improvement, Last Man Standing and The Santa Clauses, the same cannot be said for his friend Tim Allen. Allen has been doing stand-up for decades, so a foul mouth is to be expected, but according to Dunham, this also includes a rather “dark” sense of humor.

I caught up with Jeff Dunham to discuss his Valentine’s Day special, Jeff Dunham: I’m With Cupid. While discussing his various television appearances, which included a guest spot on Last Man Standing, Dunham told me this story that properly exemplifies his friend Tim Allen’s way of “testing” folks.