Man's Best Same Sex Companion was the nineteenth episode of Season 2 of The Drew Carey Show, also the 41st overall in the series. Written by Joey Gutierrez and Diane Burroughs, the episode was directed by Robert Borden. It originaly aired on March 5, 1997 on ABC-TV.
After exploiting Winfred-Louder's same-sex insurance benefits for his dog Speedy's surgery, Drew enlists Oswald to pretend to be his companion in front of the store board to save his job. Special Guest Star: Nan Martin as Mrs. Louder.
During a trip to the vet, Drew finds out Speedy's hip problem is getting worse However, there's hope in a new operation that could restore the dog to his old self. The problem is the operation costs $2,700, but Drew vows to find a way to come up with the money.
Nora learns about the situation and recommends Drew use his company insurance to pay for it. Winfred-Louder has same-sex health benefits; all Drew would have to do is claim the operation is for his "same-sex lover". Drew agrees but ends up having to prove he is gay by hiring Oswald to play his lover "Aaron".
Speedy undergoes a successful operation. Unfortunately, Drew's claim comes up on Nora's day off, and the board doesn't believe that he is gay. They insist that they must meet with Drew and his "gay" lover, "Aaron". Drew convinces Oswald to pose as his boyfriend. They fail miserably when quizzed separately about each other's likes and dislikes (other than beer and pizza), but their subsequent bickering convinces Mrs. Louder that they are a couple after all.