Based on a play by Gladys Hurlbut and Emma Wells, a middle-aged couple decides to take separate vacations to experience freedom.
Henry Smith (Frank Morgan) rents a Don Juan costume for a ball. Their maid Whiffen (Margaret Hamilton) tells Ellen Smith (Genevieve Tobin) that her husband Henry is numerically affected by 5s now. Young Frances (Betty Grable) from next door makes Henry feel old. Henry and Ellen return from the ball with Frances and Freddie (Glenn Anders). Henry asks Ellen if they are too familiar. He wants a change and suggests going away alone on a vacation for a week; they each will have $400 to spend, and Ellen agrees.
Henry invites his secretary Florence Purcell (Lorne Andre) to a show and learns she is married. Henry drinks alone at a bar and meets tipsy Skeets (Gene Lockhart), who is on the loose. Skeets takes Henry to a show to meet Gloria Dawn; but she is busy. Whiffen tells Ellen to do what Henry is doing. Ellen meets Laura, who takes her to lunch with David Mackenzie (Neil Hamilton), who shows her African love-beads. David invites Ellen to his lecture. Henry wakes up with a headache and finds Skeets in the other bed in a New York hotel. He and Skeets go to meet Gloria Dawn, and Henry meets Merle; but she doesn't like him and leaves. David talks to Ellen after his lecture, but she declines dinner.
Freddie calls a hostess for Henry from an ad. He tells Henry to get a silk dressing-gown, champagne, and a bank of flowers. Andree (Marian Nixon) arrives, and Henry takes her for a drive. Freddie calls on Ellen. Henry tells Andree about insurance. Ellen asks Freddie to leave when David calls. She invites David and says good-bye to Freddie. Henry and Andree go back to Henry's room. They drink, and he orders dinner. Andree says that Henry is not the physical type and analyzes him psychologically. She likes to comfort men. When she goes into the bedroom, Henry leaves. David shows Ellen his yacht and says she is lovely.
Henry comes home. Whiffen says Ellen is in New York. David sends Ellen a sun helmet and calls on her. He wants her to explore with him and puts the beads around her neck. Freddie tells Henry that Andree has disappeared, and she calls she is coming. Ellen comes home and goes upstairs. Andree comes in to find out why she failed. Henry tells Ellen that Freddie is engaged to Andree. Henry says his vacation was a flop, as he was scared by a woman. He becomes jealous of Freddie. Ellen says she was hurt at first, and he agrees. He bought the bathroom tiles she wanted. Ellen calls David and cancels the tiles, because her husband's are better. She gives Henry the helmet and Whiffen the beads. Whiffen cooks Henry's favorite foods, and all three are glad their foolishness is over.
This comedy of a mid-life crisis is ironic because Henry who wanted romantic success failed, while Ellen succeeded in spite of herself. Yet each realizes they love each other and are happy.