Grammar Giggles – Happy Bosses’ Day! By firstname.lastname@example.org | October 17, 2016 - 6:10 AM |October 16, 2016 Uncategorized I noticed when I was looking for a graphic for Boss’s Day that it is a confusing to the general populace. Do you have just one boss? It is the singular Boss’s Day. More than one? It is the plural Bosses’ Day. Follow Bookmark the permalink.