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Dobie and Maynard are working as 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.

After the countless times Zelda has tried to make Dobie hers, he finally gives in. Dobie is stunned when Zelda turns him down. Dr. Burkhart is trying to get class started but Dobie and Zelda are interrupting. Zelda says she's finally realized that Dobie will always be a dead weight that she will have to pull along. Zelda tells Dobie he's just too dumb for her. Suddenly a beautiful girl comes in the room and introduces herself as Claypool. She just came to town because her father's business keeps them moving a lot. He makes a lot of money building bridges. After class, Claypool tells Dobie that he may go steady with her. Now Zelda wants Dobie back and Dobie picks her. Dobie confesses to Maynard that he doesn't love Zelda, but she can help him through life. Zelda wants to teach Dobie how to think. It doesn't go well and Zelda leaves Dobie again. Claypool agrees to take Dobie and she wants to meet his parents. Claypool arrives at the grocery store riding a small elephant. Zelda wants Dobie back. He's tired of the back and forth and is staying with Claypool. But then he picks Zelda. After they decide to just be friends, Dobie goes back to Claypool, but she has now picked Maynard. Claypool moves away. Maynard and the elephant move in with the Gillis'.

Clarissa Osborne tells Chatsworth that their entire fortune of $30 million has been wiped out. Chatsworth pressures Maynard and Dunky into raising money for a needy family in town. He won't say who the family is. Chatsworth gives Maynard a Charity Wishing Well stand to collect the money. The money collecting is going very well. Dr. Burkhart brings money collected from the faculty. She says the Dean is running a raffle with the proceeds to be given to the charity. When Dobie learns what Maynard is doing and that Chatsworth is behind it, he becomes very suspicious. Dobie, Dr. Burkhart and Herbert bring Chatsworth to see Clarissa. They question Chatsworth's motives and don't believe there is a needy family. They are surprised to learn that the Osbournes are the family. They won't pursue the matter if Chatsworth gives back all the money. Herbert also wants the $16 he spent for the paint for the signs that were put up. To pay Herbert, Clarissa says she'll take a job as the Gillis' maid and Chatsworth will be the butler. Clarissa orders new appliances for the kitchen and hires a chef. Then she gets other fancy things. Herbert realizes he'll have to pay for everything and it's more trouble then it's worth. Mr. Nichols (Richard Clair), a tax assessor, comes by and Herbert tries to make things look poor. When Nichols sees all the fancy items and a maid and butler, he raises Herbert's taxes. Clarissa learns that an investment came through and she now has $35 million. Eddie Applegate as Walter Funk.

Dobie tells us how Maynard and Zelda came to be standing in front of the Justice of the Peace (Burt Mustin) getting married. At Zelda's 21st birthday party, she mentions how she would like to marry Dobie. Dobie is still not interested. Zelda says she has a plan to use Maynard to get Dobie to marry her. Maynard loves his freedom and Dobie wouldn't let that be taken away from him. If Zelda gets Maynard to propose to her, Dobie would have to step in to save him. Zelda finds a way to talk Maynard into proposing to her, not letting him know her real plan. Dobie tries to talk Maynard out of marrying Zelda. But Maynard now sees marrying Zelda as the best thing for him. Dobie can't break his heart by telling him Zelda's real plan. Even Winnie and Herbert can't find a way to get Maynard to change his mind. Zelda buys a wedding dress and has a bridal shower. It's the day of the wedding and the ceremony is starting. Dobie tries to stop the wedding, but it's Zelda that finally admits she tricked Maynard. Maynard still wants to get married. But then he changes his mind because he knows Zelda will always be wishing it was someone else. Zelda wants to continue the ceremony because she wants someone to take care of. The Justice of the Peace realizes the two aren't meant for each other and stops the ceremony. Linda Henning as Elsa.

The Osbornes are holding their annual two-day charity bazaar. Dobie and Maynard volunteer to help with things. Being short of funds, Chatsworth approaches Dobie with a scheme to get some money. Because it would be dishonest, Dobie isn't interested. But then Dobie meets Chatsworth's beautiful cousin, Pamela Osborne (Barbara Babcock) and the two immediately like each other. Chatsworth tells Dobie he'll need a lot of money to take Pamela out. Against his better judgement, Dobie accepts an offer of $50 from Chatsworth. Dobie spends the first day of the bazaar with Pamela. But thanks to Chatsworth, Dobie squanders all of the $50. Pamela talks all about the expensive things she wants to do on the 2nd day of the bazaar. Chatsworth approaches Dobie with a scheme to rig the raffle at the bazaar and split the $5000 prize. Because he already owes Chatsworth and he needs more money for Pamela, Dobie feels he has no choice. Dobie has a fantasy about a future where he and Pamela have a lot of money from all the crooked schemes he's pulled. Herbert and Winnie want nothing to do with their thieving son. Chatsworth, as the Devil, comes to claim Dobie's soul. Back to reality, the number Dobie is holding is called in the raffle. Knowing that it was rigged, Dobie doesn't respond. Pamela is stunned that Dobie is throwing away the money. Another number is called and Pamela leaves him. Dobie learns that Maynard detained Chatsworth and his number was legitimately called. Grandon Rhodes as Auctioneer.