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Gildersleeves pursues his romance with Paula. Although he sees Paula’s daughter Babs is a roadblock, Leroy thinks she’s kind of cute. Gildersleeve’s had some plans though to leave Babs at home while he takes her mom out to a movie. Will the plan work?
In the morning, Gildersleeve’s visits Peavey for an economy size bottle of aspirin. Will his friend have any advice on being able to see Paula Winthrop alone? Elsewhere, can Leroy speak some sense to Babs and give his uncle a break? Will she lay off being their chaperone? The two youngsters make a bet on which adult will propose first.
With Bertie’s help, Leroy tries to encourage his uncle to become irresistible for his date. When judge Hooker arrives, he reminds Gildersleeve is that it sleeps you. Although was no longer practiced, it was the year set aside for the ladies to make their move and proposing to men. Might Paula be up to something and getting Gildersleeve’s to marry her? Finally on a date alone, the two lovers begin to suspect the other of setting up a proposal. How will their cozy evening alone wind up? A success, or disappointment?

