Mortified celebrates 20 years with a friendly beer-league-level competition that pits city vs city. This week, Mortified's Chicago chapter faces off against Mortified NY as well as Mortified Boston in an epic three-way battle for the coveted last spot in the tournament's semifinals.

Stories include: A 2nd grader's misguided essay aimed at making retirees go back to work and pay taxes. The diaries of a middle schooler crushing on the receptionist from The Office. Oddly religious fan letters to Katherine Hepburn.

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261: Most Mortified: NY vs BOS vs CHI