Dobie and Maynard are working a janitors in a high rise office building. They hear the siren of a fire truck and see a large crowd down on the street. Out on the ledge outside their window is a man (Richard Clair) about to jump. Dobie tries to talk the man out of jumping. Maynard then gets out on the ledge and manages to get the man to go back inside. Maynard falls off the ledge and is caught by the firemen on the street. Maynard tries to explain what happened and winds up in the college hospital under observation. At first Herbert and Winnie think it might do Maynard some good, but then they want to get him out. Dean Magruder (Raymond Bailey) is holding a hearing as to whether or not Maynard should be kicked out of school. Dr. Litweiler (James Millhollin) describes the tests they performed on Maynard and how things didn't go well. Winnie and Herbert both try to defend Maynard but it doesn't help. The hearing is over and Magruder says he will make his decision. Dobie comes up with a plan to get Maynard out of the hospital and it almost works. Magruder wants Maynard out of school. Dobie manages to get Magruder to change his mind. Later, Maynard and Herbert wind up in a situation where they try to stop the same man from jumping off a pier.

Thalia Menninger (final appearance of Tuesday Weld) wants a list of Dobie's assets and net worth before she'll let him propose to her. Dobie tells her that he made her the beneficiary of his GI insurance policy worth $10,000. Thalia says that doesn't do her any good as long as he's alive. Dobie is late for a class and Thalia tells him a short cut, which turns out to be a firing range. Dobie then overhears Thalia offer Maynard some money to do something. Things start happening to Dobie and he believes Thalia and Maynard are plotting to murder him. Dobie then hears what sounds like Herbert and Winnie planning on helping Thalia. Dobie sees Herbert sharpening a large knife. What Dobie doesn't know is that Thalia just wants him to go out west where he has better prospects. And she's planning a going away party at the old Osbourne hunting lodge. Winnie suggests that Herbert take Dobie duck hunting. Herbert wakes Dobie up while holding a rifle and Dobie jumps out a window. Dobie goes to the police and talks to Sgt. Lafferty (Dennis Patrick). Dobie says that his family and friends want to kill him. Dobie wants Lafferty to stake out the hunting lodge. Lafferty says he will, but he really won't. It's the night of the party and all the guests are there. Everyone hides when they see Dobie and Thalia coming. Dobie winds up alone in the dark house and gives the signal for the police, but no one shows up. Winnie, Herbert, Thalia and Maynard show up and Dobie is frightened. Dobie finally finds out about the party. Dobie tells Thalia he isn't going out west and they break up. Paul 'Mousie' Garner as Short Policeman. Kelton Garwood as Officer Fogarty.

Herbert is thrilled to see his brother, Timothy Gillis (Ollie O'Toole). Tim travels a lot digging oil wells, so he doesn't get to visit often. Tim wonders if his son Duncan can stay with Herbert as Tim has to go to Africa. Herbert is not happy about the prospect of having a teenager in the house. "Dunky" comes in the store with Clarissa Spangler (Ahna Capri), a girl he just met outside. Dunky immediately starts to drive Herbert crazy. Later, Dunky asks Dobie's advice on how to win over Clarissa. Dobie suggests that he find some family tragedy to appeal to Clarissa's sympathy. Cathy Morin breaks up with Dobie. Dunky leads Clarissa to believe that Dobie is an alcoholic. Clarissa is now very interested in Dunky. Dunky confesses to Dobie what he told Clarissa. Clarissa told Miss Donna Whittaker (Ellen Burstyn), a social worker, about Dobie and Donna is coming by to help Dobie. Donna arrives and Dobie is immediately taken with her. Donna mistakenly believes that Herbert and Winnie are encouraging Dobie's drinking. Donna and Dobie spend a lot of time together as she "rehabilitates" him. The two wind up liking each other. Clarissa breaks up with Dunky because Dobie is now cured and there is no more tragedy. Dunky tells Clarissa that Dobie is now addicted to gambling. Hank Ladd as Drunk. Albert Cavens as Waiter.