Visiting the barber shop, Gildersleeves announces to the guys that he is interested in asking Eve Goodwin to marry him. Peevey, Judge Hooker, and Floyd all pipe in with reactions. Cigars are passed around, and well wishes received. Floyd shares how he came to propose, and his theory behind marriage. What about Peavey? Well he wouldn’t say it that way.
At home, Marjorie and Birdie work on a cake. Leroy on the other hand is so upset he wants to punch somebody. His uncle’s marriage to the school principle changes his whole school dynamic with his friends. Will the family share what they really think of the engagement with Gildersleeves? Everybody thinks its… just fine? Leila Ransom, Gildy’s former girl friend pops in. Emotions run even more awkward and tense. It isn’t beneath the fickle Gildy to flirt a little.
Before Eve Goodwin is to arrive, Gildersleeves calls Leroy aside to get the honest truth of what he thinks of having his principle as his aunt. Will Leroy be old enough to understand all the things Gildy wants to tell him in this man to man chat? Eve meets the family, and enjoy dinner together. Should Gildy and Eve duck out of the party that Leila has planned for them? Meeting obligations to friends, the girlfriends, old and new, compare notes on Gildy’s dating habits. Will the embarrassing moment cause a rift, or cement a relationship?