After Ricky's Badger Patrol leader pulls out at late notice, he and Kate convince Edward to take the boys to the national convention in Chicago. While there, Derek and Ricky hatch a plan to get lucky with some high school cheerleaders.
Ricky has his friends Derek, J.T. and Freddy for a sleepover, but the boys play a cruel prank on Freddy - and Ricky makes it worse with a selfish remark. He feels guilty about his behavior, while Kate over-identifies with the taunting.
Rick tries to change to a more edgy image in order to impress some girls - but when they pressure him into things he doesn't want to do, life on the edge starts to make him uncomfortable.
Despite the previous night's kiss, Edward and Kate start to feel defensive about their romance. When they both arrange grudge dates to make each other jealous, Ricky schemes to have his father crash Kate's date at Carnegie Hall.
Rick writes a computer program to predict football scores, making bets along with his friends. But when he ends up indebted to a bookie, he steals a rare coin from his father's collection.
Ricky gets his first taste of puppy love when a new girl transfers to his school. He also probes Edward about his romantic interests, just as Kate leaves for a singles cruise.
After getting in trouble in class, Ricky sets out to win the 8th-grade science fair - with a little help from Kate, who is trying to prove a point with Edward.