Regretfully remembering his dismal date with Arlene Nestrock before her family moved to New York, Richie does a successful do-over when she comes back three years later and winds up going steady before he's ready.
Having to drive the Cunningham family car and a run-in with a gang stack the odds against Richie and his buddies after Bag Zombrowski challenges them to come up with dates by midnight or walk through popular Arnold's parking lot in their underwear.
Richie gets an in for an interview with famous children's entertainers Bob Smith and Howdy Doody when little sister Joanie appears on the television show to present the popular puppet with the Chipmunk of the Year Award. But Richie is later confronted with an ethical dilemma after Life magazine offers to buy his one-of-a-kind photo of clown Clarabelle caught without his makeup.
Richie is called upon for a favor by an old friend from summer camp (possibly older than he),who is now the member of a successful rock and roll band called "Fish and The Fins". While they're in town he wants to use Richie's home for the band because they can't rehearse with groupies surrounding their hotel. He has to keep it quiet though. Before this,Richie already told people he knows leader, Rocky Rhodes, and has guaranteed his friends free concert tickets. Which end up being in the "rafters" so Richie's rep. is on the line! Will Rocky be able to redeem Richard's ...
While in Chicago with their high school choir, Richie, Ralph and Potsie sneak by their chaperons, wind up on the wrong side of an unsympathetic downtown nightclub owner, and win the sympathy of a kind-hearted cocktail waitress.