When Billie Jo has to come up with a fourth for her double date with Junior Hocker and Junior's visiting friend Roger Budd, Kate suggests Bobbie Jo to her. Billie Jo doesn't think Bobbie Jo would be a good fit as she knows all the boys see Bobbie Jo as a book worm instead of a fun girl. Convincing Bobbie Jo may be more difficult as Bobbie Jo admits that she just doesn't feel comfortable around boys yet. She goes on the date, but comes home early saying she just can't compete with Billie Jo. Kate tries to teach Bobbie Jo how to flatter a man the way Billie Jo does. On her next date with Roger, things go much better.

Kate and the girls go to Drucker's store to pick up the pocket watch they ordered for Uncle Joe's birthday present. While there Kate, in an effort to boost Herby's confidence, inadvertently offers him a job as Assistant Manager at the hotel. Now Kate doesn't have the heart not to give him the job, so she decides that she can give him some menial tasks at the hotel. Uncle Joe believes he is being put out to pasture with Herby showing up. He goes in search of another job. He gets one, telling everyone that he is an executive with some large company. Kate follows him and finds out his big job is actually mopping floors in a cafe. Kate and Sam have to figure out a way to get both Herby and Uncle Joe back to their real jobs.

Herby is depressed when he gets drafted, so the girls cheer him up by suggesting he could be an astronaut. Uncle Joe hears this and decides he needs to promote Herby's future political career to the whole town. When Herby gets a discharge for minor medical problems, Kate finds a way for him to save face with Billie Jo and the rest.

Billie Jo is still determined to use the $500 from her father to go to Hollywood to become a movie star. It doesn't help that Uncle Joe, who wants to go with her, is fueling her dream. Kate talks with Judge Drucker to see if she can legally prevent Billie Jo from going to Hollywood, but he advises against it. Dr. Depew believes Kate's mistake between Dr. Harris and Billie Jo was throwing them together in a professional relationship. He thinks they should throw them together in a doctor/patient relationship. First, they have to trick Billie Jo into thinking she's sick. Then, they have to get Dr. Harris to come by each day to check on her. Kate believes there is one more piece to complete the puzzle, courtesy of a fake edition of the Hooterville World Guardian.

A regional talent contest is being held in Hooterville with the winner being awarded $50 and a trip to Chicago for the television broadcast final. Kate worries that competition among the girls will affect the family. Uncle Joe has other thoughts where he wants the girls to compete their hearts out with the goal of winning. The girls agree in that they figure Kate could use the $50. With the ulterior motive of being the adult chaperon for his winning niece in going to Chicago for the final, Uncle Joe tries to convince all the credible competition not to enter the contest. Kate wants the contest to be fair and undoes all of Joe's scheming. After their performances, the girls decide they were only thinking of themselves and drop out of the competition.

An old school chum named Emily Mapes thinks it's time Kate was married again. She tells the girls to round up some prospects to go to the Shady Rest to court Kate. The girls do this by offering special rates to single men. However, Uncle Joe thinks that if Kate finds a man, he will lose his job. Joe even pretends to be the house detective and tells guest Grover Woodstock to leave Kate alone. Kate finds out from Grover what her daughters have been up to. She comes up with a plan with all the men to teach her girls a lesson.

Mr. Bunce with the bank is doing an inspection of the hotel and is not planning on extending Kate's financing. Wealthy socialite Clara Watkins checks into the hotel with her son Sonny. Bunce will only extend Kate's financing if Mrs. Watkins recommends the hotel to her friends. Meanwhile, annoying Sonny is constantly chasing after Billie Jo. Mrs. Watkins wants the two of them to get married. While Kate has done whatever she can to please Mrs. Watkins, she has to say no to that. Uncle Joe decides to romance Mrs. Watkins instead and she soon accepts his marriage proposal. Kate comes up with a plan to save Joe and the hotel.

Homer Bedloe arrives at the Shady Rest with his son, Homer Bedloe Jr., who is as hateful and devious as his father. He even looks like his father down to the horn-rimmed glasses. Bedloe Sr.'s plan is that he wants to appear the loving and caring father, bringing his son up right. Then he will leave Jr. alone at the Shady Rest to snoop around and find a way to shut down the Shady Rest and the Cannonball for good. But Jr. comes to like everyone because he is treated with kindness and goodwill for no apparent reason.