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.

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.

Uncle Joe wants to dig out an old cave to use as a wine cellar for the hotel. Kate receives a telegram from Brooks T. Webster, who wants to possibly hold a convention at the Shady Rest. He will be arriving that afternoon. Uncle Joe causes a landslide covering up the cave entrance with Kate inside the cave. They will need Ding Woodhouse's tractor to remove all the rubble to get Kate out. But Ding's tractor needs some work done on it and won't be ready until the morning. Mr. Webster arrives and insists on dinner, but Kate isn't there to cook. Uncle Joe comes up with a plan to feed Mr. Webster and get the convention business. But is Mr. Webster the only one they need to impress?

Kate has sprained her ankle which means she will be off her feet for three or four days. Now that Mr. Webster's gone, the family has to prepare for Mr. Feasel's visit. He is the one that will decide if the convention will be held at the Shady Rest. Uncle Joe decides to make some changes to the hotel he's sure will appeal to conventioneers. He also hires Smokey Harner, a country singer and guitarist. Hearing about all the new ideas, Kate believes Uncle Joe and the girls may be running the hotel better than she did. Mr. Feasel arrives early and is not impressed with anything about the hotel. Kate recovers quicker than Dr. John Rhone expected. But she wants to keep her recovery a secret because she thinks everything is running smoothly and wants the family to feel good about themselves. With everything going wrong in the hotel, Mr. Feasel leaves. Kate finds out that Feasel has left. But he later returns for a very unusual reason.