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Michael sums up his feelings for Toby in the episode "Casino Night", asking, "Why are you the way that you are?Honestly every time I try to do something fun or exciting, you make it not that way.He also has a long-standing crush on Pam Beesly, which he almost reveals at the end of Season 4 when he resigns from his position to move to Costa Rica.
Toby Flenderson is the human resources representative for the Scranton branch of paper distributor Dunder Mifflin/Sabre.Toby prefers to let angry employees vent to him, after which they feel better and the conflict eventually settles down and solves itself. Toby usually avoids office activities whenever possible and, like most of the staff, only tolerates Michael.This strategy worked virtually trouble-free for years until Michael Scott publicly reads off all listed complaints. He has reached out to Michael several times despite Michael's continued abuse. When Dwight approached Michael about missing a gift bag during "A Benihana Christmas", Michael suggested stealing it from Toby, much to Toby's later chagrin, as all the office staff had new robes except for him (Pam later gave her robe to Toby, and this increased Toby's unrequited crush on her).Toby tries (but usually fails) to enforce corporate policies and rules when Michael disregards them, typified by an incident in which he quashes Michael's plan to invite Boy Scouts to a Casino Night party: Actually, I didn't think it was appropriate to invite children since it's, uh, you know...there's gambling and alcohol..it's in our dangerous warehouse...it's a school night, and you know, uh... Michael on numerous occasions attempts to blame Toby for problems that are clearly his own fault such as in "The Merger" in which he questions Tony Gardner if he is quitting is because of Toby.In "Classy Christmas" Michael vandalizes Holly's Woody doll (a gift from her boyfriend) and tries to convince her Toby did it.