Tony fears he can't afford the ski club Samantha wants to join with her friends, but he lets her sign up anyway. When his attempt to economize by cleaning Angela's chimney himself fails, he must go back on his word and tell Samantha she cannot join. Refusing to borrow the money from Angela, Tony soon sells one of his prized possessions to be able to pay for Samantha's ski trip.

Samantha has just begun junior high school, and has little trouble becoming friends with the popular girls. Since they are all from wealthy families, Samantha is afraid they will not like her if they know of her true past, so she tells them that Tony owns Angela's house and is an advertising executive.

When Samantha needs more money to participate in activities with her basketball team, Angela hires her to work for her on Saturdays. But Samantha soon realizes that, by working weekends, she is missing all the events she wanted money for. So she decides to do a poor job, hoping to get fired.

A sitter's last-minute cancellation leaves Samantha to watch Jonathan while Angela and Tony go to a parents' meeting at school. Samantha panics when Jonathan inadvertently tosses a piece of jewelry down the sink drain. Although Tony had told her not to have any guests, the house is soon full of her friends: Chad, a boy who thinks he can retrieve the missing jewelry, and four of Samantha's friends who come to admire Chad. Tony and Angela return home just as the kids are sneaking out.

Marci applies for the elite-school Montague. Sam also wants to do so and finds an advocate in Angela, a Montague Academy graduate. But Tony doesn't like the idea that Sam visits a school so far away.

After a party Sam comes home with a love bite and Tony, beside himself, forbids her seeing Todd again. In the evening Sam sneaks out of the house to meet Todd anyway.

Dr. Ferguson, Marci's Dad, marries and Tony and Angela should be best man and maid of honor. In the course of this both have to face the question whether the want to marry again. At the wedding party they meet Geoffrey.