Mr. Boynton injures himself on Mr. Conklin's property and Miss Brooks devotes herself to his hospital recovery. Conklin is concerned about being sued and needs Connie's assurance that she mailed his insurance check in.
Connie Brooks owes $.20 to a recently retired postal clerk Mr. Bagley. He seems to have disappeared so the intrepid teacher turns herself, Mr. Conklin and Mr. Boynton into detectives to find him but gets a big surprise.
Mr. Conklin's garage explodes and he gets the idea that Connie has carpentry skills. He puts her in charge of constructing a new building, so she enlists Walter and Philip to help. The result has an unexpected conclusion.
Mrs. Davis is arrested for selling charity tickets that are actually fraudulent. She visits her sister without telling Connie about the tickets who prints more, then gets everyone thrown in jail when they try to sell them.
Connie agrees to put up Philip's jockey friend Billy and his horse before a big race. Owing money he needs to lay low so Connie, Philip and Walter must convince Mr. Conklin he's losing his memory and that Billy is a new student.
Miss Brooks buys a used car leading to a series of improbable mishaps involving a fruit stand, a little red wagon, and various automobiles. The damaged vehicles always belong to Mr. Conklin and Connie's debt increases.
Miss Brooks learns that Harvey Brent has given a false address and goes to investigate. She meets his father plus two friends who are raising the excellent student in a makeshift home and tries her best to keep him in school.
Walter decides to start early with April Fool jokes and convinces Mr. Conklin he's won a TV. Osgood tasks Connie into picking it up, leading her and Philip on a wild trip laid out by Walter. Conklin somehow ends up with three stolen "prizes".
Connie is assigned by Mr. Conklin to show an attractive Mr. Philpott, a visiting British teacher, around. Connie uses the opportunity, with Walter and Angela's help, to advance her romance with Philip.
Miss Brooks is ordered by Mr. Conklin to tutor a few struggling students so they won't bring down the school's average. But the time coincides with what Connie hopes is a special date with Mr. Boynton.
When Osgood wants Connie to assume the first aid duties of her nemesis Enright so Enright can work part-time, Walter proposes she fake incompetence to avoid the task but the plan goes awry when Boynton appears.
At breakfast Connie and Walter wonder if an egg is fertile, taking it to Mr. Boynton for an answer. Mr. Conklin thinks it's hatching would be a great photo project and sets up a watch. He learns too late Walter switched a rock for the egg.
Miss Brooks learns a woman from Philip Boynton's past is in town and is extremely curious. Her only clue is the lady is connected to the bakery so Connie investigates, trying not to be caught but fails miserably.
As summer approaches Connie learns she can get a free European vacation if she can enlist three others to be paying customers. But everyone she approaches secretly has the same idea but to other exotic locales.
Mr. Conklin's bicycle is taken from the grocery story and he wants the thief punished. But Miss Brooks learns a poor lad only borrowed it for his birthday and has returned it. Connie goes to elaborate lengths to protect the boy.
Connie and Philip are applying as tutors for a hillbilly show for extra summer cash. They must double as entertainers so they enlist Walter and Mr. Conklin as awful stereotypes, then accidentally audition for the state education official.
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 High entices the young man to their school so Connie and Mr. Conklin pretend to be his parents, with Walter as Stretch, to 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.
Walter pranks Mr. Conklin by putting a BB in his telescope after he has to polish it. Osgood believes he's discovered a new planet. Miss Brooks keeps the secret to spend time with Mr. Boynton who's enthusiastic about astronomy.
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.