Bentley meets Julie Corey, the daughter of a friend of his and notices how polite and proper she is and realizes Kelly doesn't quite meet that same standard of social graces. Bentley learns about a finishing school that Julie attended and begins thinking of sending Kelly there. However, Kelly doesn't like the idea at all but agrees to go to the school anyway but little does Bentley know that it is a plot that Kelly has concocted and has enlisted the aid of Peter to outwit her uncle.
Kelly urges her Uncle Bentley to try out for the leading role in a forthcoming production of Cyrano De Bergerac that is being put on by the PTA. Bentley allows himself to be persuaded but during the rehearsals he argues with the leading lady, Diana Webster, and walks out on the play. Having second thoughts, Bentley tries to patch things up with Diana, but she refuses to even take his calls and Bentley finds himself pushed out of the play completely but an emergency on opening night may be what Bentley needs to get back in.
Everyone has plans for the same weekend: Bentley decides to take a weekend vacation to Mexico while Peter plans a trip to San Francisco for a birthday party and Kelly is excited about plan to go to the mountains. However, everyone's plans hit a snag when they realize they have forgotten about Jasper, the family dog. After mulling over options and initially against it, Kelly agrees to have Jasper placed in a kennel, but this simple solution turns goes awry when Jasper unexpectedly runs away.
Kelly loses her self-confidence when a teenage siren, Valerie, moves to the neighborhood and becomes the center of every boy's mind at school. Bentley does his best to try to make Kelly feel attractive but Kelly and the other girls at school decide to retaliate and decide to blackball Valerie. Meanwhile, Bentley encounters Valerie's father, a braggart, at the gulf club, who sheds some light on Valerie's situation and Bentley soon encourages Kelly to befriend Valerie rather than make her an enemy.
Bentley gets fed up with Peter leaving him notes and messages that he cannot decipher and insists that Peter take a night course in English. Although hesitant at first, Peter enrolls in night school but soon Peter goes overboard and takes as many courses as he can and begins to neglect his housework. Bentley becomes resentful of Peter's teacher, Miss Cutler, whom Peter raves about, that is until Bentley meets her and she catches his romantic eye.
Ruby Polk, the wife of an important client decides that Bentley would be the ideal husband for her plain niece, Lucille. Ruby soon begins playing matchmaker doing everything that she can to get the two of them together. However, Lucille only has eyes for another man and Bentley does his best to get Lucille together with her true love and not let Ruby ruin her happiness. So he plans a secret wedding at his home but Bentley gets an unexpected crasher, Ruby.
Bentley has a meeting with his client, Ronnie Burns who believes that an ex-girlfriend, Lorraine, is stalking him and not only that but also has her jealous ex-boyfriend Fred is after him as well looking for revenge. Meanwhile, Kelly is invited out to dinner with Bentley and Ronnie and she comes down with a massive crush on Ronnie and talks of nothing else and fails to realize reality when she herself encounters Lorraine. Meanwhile, Bentley and Peter do their best to try to break the love spell that has come over Kelly.
Bentley is asked by a wealthy client to represent his wife in a minor car accident that resulted in a dented fender. However, Bentley soon realizes that there is a lot more at stake, when he learns that Peter is on the opposing side, acting as his own counsel and refusing to settle for the $18 in damage or back down from his principles. Meanwhile, Kelly has a tough choice when she is torn between standing up for an unpopular girl or running for club president.
Bentley decides to place the household on a stringent budget, but with very unhappy results.
Kelly finds herself in a bind when she gets two separate invitations to attend the prom. As Kelly begins debating which boy should like to go with, she asks Bentley's advice. He soon finds himself being the person to turn to for advice, Peter turns to him with stock market advice and Kitty turns to him for wardrobe advice, but he becomes convinced he is cursed when all advice that he gives turns out to be bad. Meanwhile, Kelly's decision goes awry and she just may find herself without a date for the prom.
Kelly has been content with life since moving in with Uncle Bentley, however she quickly realizes, Bentley has been putting too much time and effort into her life and wants to discourage Bentley from checking up on her every move, so she decides to give him something big to worry about. She pressures her boyfriend, Howard, into taking objects from the Gregg household, creating the impression that the young man is a kleptomaniac.
Bentley staunchly refuses Kelly's plea for a second telephone in the house. But Kelly is determined to make him change his mind.
Kelly's boyfriend, Howard is always hanging around and Bentley reasons that if Howard's singing career took up more of his time, Bentley would see less of him. So Bentley decides to give Howard's career a push.
Kelly has a crush on a boy who suddenly takes an interest in a young bubbly girl who giggles at the drop of a hat. This convinces Bentley that Kelly should try to become more popular with boys and try to alter her personality. Meanwhile, Bentley joins a committee to put together a school carnival and Bentley becomes determined to get Kelly named the queen of the carnival and finds himself competing against a fellow father who is also determined to win.
Concerned over Kelly's lack of discipline, Bentley decides she needs a woman's guidance. He sends for his Aunt Caroline, whom he hasn't seen in twenty years and who he remembers as being very traditional and motherly, but her arrival only complicates Bentley's problem when Bentley learns that she has become very worldly and adventurous and she invades the Gregg household and sets out to turn Kelly into a sophisticated woman. Meanwhile, Bentley begins to plot the best way to get his aunt to leave.
Bentley falls for the charms of a lovely girl who operates a health club. He is so impressed that he starts exercising with barbells and eating health foods, hoping to capture the young lady's admiration. It soon turns into a competition when another man enters the scene trying to snatch her affection as well. However, Bentley's rigorous new lifestyle begins to take its toll on him and he decides to fall off the health food wagon.
Kelly's friend Ginger is ecstatic when she announces that she is going steady and Howard decides he wants to go steady with Kelly and he asks Bentley for permission to go steady with her but he refuses on the grounds that Kelly is too young to be held down to one person. However, Kelly later comes home with the news that a boy has asked her to go steady and Bentley adamantly refuses to let her especially since it is the same boy who ran him off the road with his motorcycle and whom Bentley considers a juvenile delinquent.
Bentley is planning a trip to New York and is planning on taking Kelly and Peter with him. Beacuse he is planning on an extended stay he decides to rent his "bachelor pad" and hires a realtor to find someone to rent. However, when plans change, Bentley finds himself without a place to stay when the family who is renting his California home refuses to leave which forces Bentley, Kelly and Peter to find a way to force them out.
Bentley takes an avid interest in a beautiful Peruvian girl and helps her to win a talent contest. But he encounters unexpected complications in his campaign to woo her.
A girl who has her heart set on breaking into pictures decides that Bentley is just the man to help her. The girl begins by pretending to drown so that Bentley can save her.