Ryan is the newest addition to Dunder Mifflin as the temp in Season 1 and witnesses Michael’s inappropriate sense of humor when he fake fires Pam, leaving her in tears. Michael lavishes Ryan with unwanted attention and has a severe mancrush on him, but Ryan finds Michael annoying and does his best to ignore him, unless it benefits him.

When Ryan begins dating Kelly, he again finds himself receiving unwanted affection and attention. Ryan is cocky, arrogant, and desperately trying to prove how smart he is. Season 4 sees him promoted to Jan’s old position and he becomes Michael’s boss, but that didn’t last long because he’s arrested for fraud and is fired from the company.

He had to work in a bowling alley until Michael offered him a job with the Michael Scott paper company. Later, he rejoins Dunder Mifflin as a temp in “Weight Loss” and he gets some good hazing. After Season 5 his personality seems to change from episode to episode from bow tie wearing hipster to scarf wearing poet. No one, including Michael, take him seriously anymore.