Mr. Pomfritt assigns an essay addressing a big question: "Whither are we drifting?" Dobie and Maynard mull the question and their uncertain futures in an atypical episode that is more thoughtful than humorous.
Dobie encourages Zelda to go and be wined and dined while tutoring the Yale-aspiring Chatsworth (thus freeing Dobie to date other girls). Will it be "out of sight, out of mind" or will Zelda's absence make his heart grow fonder?
Central High's yearbook editor Zelda assigns Dobie and Maynard to write a "where are they now" feature on the school's former star football player and 1911 graduate Walter "show 'em no mercy" Appleby, whom the boys discover has seemingly fallen on hard times.
Mrs. Gillis writes the winning entry in a contest and Dobie eagerly anticipates the prize: a date with glamorous movie starlet Merilee Maribou. Seeing the date as a stepping stone to success, Dobie performs "Don't Shoot The Man on the Moon" from Dwayne Hickman's 1960 Capitol LP, "Dobie."
Dobie's upcoming graduation brings to light the embarrassing fact that Herbert T. Gillis never graduated high school, but thanks to evening classes for adults Dobie's Dad is determined to finally finish what he started long ago.
Dobie receives a friendly letter from his Uncle Sam: "Greetings. Your enlistment in the United States Army has been processed." As the Gillises prepare to send their boy into the service, Dobie's baby shoes spark a flashback to the 1940s when Mr. and Mrs. Gillis were eagerly expecting their baby.
After getting his beard caught in his rifle's bolt release, Maynard is ordered to shave off the offending fuzz. When the protest cat protests the order, Dobie defends his friend before a military tribunal.
Dobie, Maynard and Corporal Kilroy (a chimpanzee) are selected to participate in Operation Moonshot, which experiment requires them to spend 30 days in a simulated space capsule. Will Maynard and Kilroy's antics bring them from the frying pan to the launching pad?
Dobie and Maynard land the lead roles playing officers in Lt. Merriwether's play. Following a rehearsal and still dressed as his character Major Gates, Dobie meets and woos with war stories a beautiful young lady who's father happens to be the base's gruff new colonel. Will it be Herbie "Snow Job" Gillis to the rescue or 20 years in the brig for impersonating an officer?
After watching a sentimental war movie, Maynard is stricken with acute homesickness and secures a pass home. Dobie fears his buddy has gone AWOL and returns home to bring him back, securing his own pass home by claiming that his father is deathly ill.
Zelda tells the snooty Rochelle that she and Dobie are secretly engaged, weaving a web of deception that threatens to ensnare her at the big society party. This time the spotlight shines on Sheila James in what appears to be a set up for a spin-off.
Maynard, of whom no man could ever be jealous, suddenly finds himself a hot commodity among the coeds of S. Peter Pryor Junior College when he agrees to serve as their escort to social events while their boyfriends are away. Dobie, fearing his caviar-stuffed friend is headed for a life of dissipation and decay, sets to rescuing him.
Dr. Burkhart asks her class to bring items to include in a time capsule, but Maynard refuses, discouraged by his conviction that within a matter of years the world will go "boom, boom, ker-boom!" and there will be nobody left to discover the time capsule.
Mr. Pomfritt reports $41.37 has disappeared from his desk. Earlier that day Maynard arrived to school in a taxi, telling Dobie a squirrel gave him $41.37. Dobie tries to right the wrong, but, proving that no good deed goes unpunished, finds himself the prime suspect.
Maynard befriends a poor Mexican shoeshine boy and generously gives him $55.78--all the money his classmates had saved to fund their Christmas dance. To earn back the money, Maynard takes a job as a department store Santa Claus.
When the irresponsible quarterback the Gillises and Maynard have been trying to help and keep from getting cut from the team disappears just before kickoff, a gridiron veteran volunteers to come out of mothballs to cover for him.