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Mr. Douglas is Chandler's boss at the company he works in. He is shown to have a very strict and serious behavior in business as he even forced Chandler to fire an employee whom he loves, Nina Bookbinder, in "The One With the Two Parts:Part 1". He also appeared in "The One With the Pox" where he hired Joey (who started to go by his new character, Joseph) as Chandler's co-worker, even though Chandler was irritated with "Joseph" ruining his life and eventually got him to quit by threatening to have an affair with the latter's alleged wife, Karen.