Connie meets Ricky, a young boy who gives the impression he's an orphan and his uncle mistreats him. Miss Brooks shares his tale of woe with Mr. Boynton and Mr. Conklin who join her in trying to help the lad who hasn't been quite truthful.
Connie is told by Mr. Conklin to pick up their costumes for a masquerade ball. She accidentally gets the incorrect outfits, getting ones reserved for an important state official and his wife who Osgood wanted to impress.
Connie is jealous of Mr. Boynton's new colleague, biology teacher Miss Sanders and their common interests. She concocts a scheme with Walter to bury butcher bones in her backyard but Walter substitutes dinosaur bones creating havoc.
Connie is involved when Madison's best athlete Stretch has to temporarily relocate. Rival Hamilton entices the young man to their school so Connie and Mr. Conklin pretend to be his parents with Walter as Stretch to stop outwit them.
Connie is helping Angela prepare for her wedding but no one has met the groom Mr. Farnsworth. Angela mistakes the new coach Mr. Greeley as her intended and becomes apprehensive. Mr. Boynton becomes jealous of the brawny Greeley.
Miss Brooks has taken up painting and her self portrait attracts the interest of Mr. Baptiste. Walter loses the painting, creates a bad imitation and Mr. Conklin decides to involve himself. He outbids Baptiste who's only interested in the frame.
Connie goes to the movie alone after Philip breaks a date but then sees him acting suspiciously after a jewelry store robbery. But it's Mr. Conklin who is arrested so Miss Brooks takes extreme measures to keep both men out of jail.
Mr. Conklin takes up astronomy as a hobby and soon discovers a new planet which he humbly names "Conklin Jr." Actually, it is a painted bee-bee that Walter Denton has put in his telescope as a practical joke!
Miss Brooks welcomes former student Terence Layton who has become a popular novelist. She decides to use his former crush on her to make Philip jealous. But it's Layton's expose of Madison High that has Mr. Conklin in an uproar.
Miss Brooks finds a four leaf clover and truly believes it will bring good luck including a promotion. But a series of calamities occur primarily involving a car she just fixed plus ruining Boynton's perfect attendance and Conklin's trip.
Miss Brooks reads from a government pamphlet that all good citizens harbor a secret. The news weighs heavily on the minds of Connie, Philip and even Mr. Conklin until they all confess their misdemeanors.
Miss Brooks gets a letter of unknown origin in which someone named "Buddy" is going to be killed. Both Mr. Boynton and Mr. Conklin think that they are the "Buddy" referred to in the letter. Miss Brooks discovers that "Buddy" is actually a bull that a friend was going to fight and kill. She uses both Mr. Conklin and Mr. Boynton's fear of the supposed murderer to her advantage though with hilarious results.
Mr. Conklin thinks he's being fired after mishearing Connie and superintendent Stone. He writes a nasty letter before learning the truth and involves Miss Brooks into fixing the problem, effecting her own English department promotion.
Miss Brooks and her friends arrive at Madison High to see that it's been vandalized. Connie and Walter learn that Stretch is responsible as he was trying to catch a gopher per Mr. Conklin's orders. They try to ensure Stretch isn't blamed.
Old friend Safari O'Toole is visiting Mrs. Davis for her birthday. She's determined to wear a ring he gave her years ago, but it goes missing. Also, everyone is broke but determined to give the Margaret a gift so the pawn shop becomes busy.
Miss Brooks is urged by Margaret and Philip to fight to get a penny back after a weight machine malfunctions. But a rumor spreads among the students that she's broke and begin raising funds for her as she continues her effort to get her refund.
School officials are visiting Madison and Mr. Conklin to give a welcoming speech. But he fears doing badly so Miss Brooks aids him by taping it ahead. But putting Walter and Stretch in charge of the recorder proves to be a mistake.
Madison High is having a fundraising campaign and a philanthropist has agreed to donate a house's contents. Mr. Conklin and Walter both give Stretch errands which he confuses. Mr. Conklin is surprised to see his furnishings being sold.
The Madison kids are hanging out at Elmer's Malt Shop instead of doing homework and Mr. Conklin is going to stop it. He hires Orville Mason as security who's actually a dance instructor. Connie and Osgood go incognito to learn the truth.
Connie dreams the impossible dream: she finally marries Mr. Boynton. In it, the two are new grandparents to the child of Osgood Conklin, Jr.
When an ex-boyfriend announces a visit, Mrs. Davis wants to impress him by pretending to be wealthy. This leads to Connie posing as her personal secretary, even as the bill collectors are knocking at the door.
Miss Brooks plans to make extra money as a waitress, not knowing that the hot dog stand is owned by Osgood Conklin.
Local landmark Kritch Cave is being sold so Connie, Walter, and Philip visit to reminisce. Miss Brooks becomes involved in the transaction, ending up with the incorrect deeds and accidentally sells Madison High. Miss Davis comes to the rescue.
Miss Brooks changes her hair style per Harriet's suggestion to reignite her relationship with Philip. Mr. Conklin, concerned about an official visit by Fosdick, tries to get her to take time off so she's not around. Instead, she greets Fosdick with strange behavior.
Stretch's prowess as a baseball player is changing expectations about his future. But an injury has Miss Brooks persuading Conklin and Boynton to pretend to be agents so the actual baseball representative will still sign Stretch.
Walter's idea to have students and teachers swope roles happens at Madison despite Mr. Conklin's opposition. Connie learns Walter forged the letter of official approval so she needs to convince Mr. Stone he wrote it.
Miss Brooks and Mrs Davis are both being stalked by a man they have never seen before. In the mean while Mr. Conklin is having a severe attack of allergies. Finally Connie finds out that the man that is stalking her is part of the "Here is your Past" TV program. They bring on her friends and fellow teachers including Mr. Conklin. The prize for Connie appearing on the show is a puppy and of course Mr. Conklin is extremely allergic to dog hair!
Mr. Conklin thinks the school needs a new mascot and his wife breaks an elephant bookend. Due to a torn note Miss Brooks and Mr. Boynton misunderstand the situation and head to the circus to get the animal they believe has been selected.
Mr. Conklin gets his name in the paper by scheduling a safety jump from the school roof. However, when the day arrives for him to jump he gets cold feet, fakes an injury and then tries to get someone else at Madison to do the jump in his place. Suddenly all of the male teachers are injured in some way and it is up to Miss Brooks to jump or else!
Connie is going to cook a meal on Mr. Boynton's new stove to prove to him that she is the "domestic type" and enlists Mrs. Davis's help (since she can't cook). Little does she know that the stove isn't properly installed and soon the kitchen full of gas, and Mr. Conklin arrives with a stuffed-up nose and a box of matches to find his toolbox in the dark kitchen. You can guess what happens next!