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Great men through the ages have always had women troubles, and the great Gildersleeves is no exception.
A montage of incidents with his dipsy secretary demonstrate his growing frustration, and desire to fire her. He is so frustrated that he has lost his appetite for breakfast. Though Marjorie and Leroy think he’s just a big softy, Gildy is determined to go through with firing Bessy.
Even Birdie is doubtful, but Gildy goes straight to the office and after a false start, he does the dirty deed, but Bessy mistakes the firing for a marriage proposal. Later Gildy avoids running into the judge, by ducking into the employment agency. They seem to have just the right match for him, but still, he needs to fire Bessy.
Rumor on the street is that Gildy is going to be fired when the Judge mistakes his ducking into the employment agency. Peavey tries to be charitable towards Gildy when he believes the rumor, but also mistakes Gildy’s touchy nature. Gildersleeve fesses up about wanting to fire Bessy, but Peavey is just as doubtful as all the rest as to his will power.
Gildy goes back to face off with Bessy, and her mistake at his proposal has touched her ethical side. She just can’t work in a place where an office romance might interfere with the daily job, so she quits. Next day, Gildersleeve tries to welcome the new secretary, Miss Lovejoy. She is impressive as she dives right into the job. With the highly efficient Miss Lovejoy on the job, Gildy pops out for a malt, and tells the judge all about it. They both decide to play hookie, and spend a day playing like Huck Finn and Tom Sawyer. Gildy tries to get Peavey to join them. Too bad Gildersleeve recieves a big disappointment when he learns the efficient secretary already has the Water Commissioner’s afternoon planned out, and won’t stand for playing hookie. Since the judge and Peavey are already sold on the idea, they take off without their friend.
Besides efficient office practice, the secretary begins to invade into Gildersleeve other habits. Cut down the trips to the water cooler, no smoking, shorter lunches. Gildersleeve begins to miss Bessy, and when he can’t stand anymore, he fires the new secretary. . At the depth of his despair, Bessy comes back with a change of heart. She’ll agree to return if he can manage to only think of her as an employee, and not someone to be married to. Of course he happily agrees.
In epilog, Gildy meets the real Mr. Morris the new secretary kept talking about. He presents Harold Peary an honorary certificate into the Water Works Association.
Note: in real life, Bessy was the real life wife of Harold Peary, the Great Gildersleeve.