Greg is jealous of Jen's handsome new assistant; Heather and Tim prank Tyler's school; Joan allows Sophia to chew gum despite Heather forbidding it; and John takes his new puppy on a date with Colleen and her dog.

Tim thinks wearing a Cinderella dress during March Madness is good luck, so he refuses to take it off in hopes his alma mater will win. Also, Greg fantasizes about what to write in a birthday card for his boss, Tyler goes to prom and must withstand unsolicited advice from his parents and grandparents, and Jen sets Matt up on a blind date with her coworker, Dougie.