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Kevin's 18th birthday is approaching and he's apprehensive for his first sexual experience. Pressure from his friends doesn't help any when they suggest he take out a girl who has a reputation for being easy. Kevin quickly finds himself in an uncomfortable situation when he takes their advice.

Kevin has begun college and decides to join a fraternity. Part of his initiation includes, donning women's clothing bringing the worst looking girl to a frat party. Coincidentally, Kevin meets a girl whom he thinks fits the bill, but wants to spare her feelings. However, he finds himself trapped and hurting her feelings seems to be the only way out.

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Marsha's position at the Legal Hut has been draining all the excitement out of her and when she's offered a higher position she secretly decides to turn it down. Little does her family know, that she has quit altogther at the Legal Hut and has taken up a position as a singing waitress at a 50's style restaurant.

For some extra money, Kevin picks up a job as an escort and after having an encounter with a sexpot, Kevin meets a sweet old woman whom he hits it off with and even begins thinking seriously of marriage when she proposes. Meanwhile, the Owens' monthly bills have gotten out of hand and Mr. Belvedere suggests a strategy to curb the family's expenses.

Kevin gets a job at the used car dealership run by Carl's Uncle Phil. Kevin at first has a hard time getting into the selling business, but quickly becomes a natural crooked used car salesman. Meanwhile, Mr. Belvedere recieves a letter from the Queen expressing her desire to have Mr. Belvedere return to his previous position.