Edward Stratton III is a toy company magnate who is still a child at heart; his giant Long Island estate is filled with expensive toys, including a train set he rides through the house. On the same day his lawyer and business manager tell him that he is on the verge of total bankruptcy, he discovers he has a 12-year-old son named Ricky - the product of an ill-fated six-day marriage - who shows up on his doorstep. The computer-savvy Ricky comes to the house from the military school where his recently remarried mother left him, and discovers that his business manager has embezzled Edward's fortune. He uses the computer to transfer the stolen money back into the company's account. While initially reluctant to let the boy live with him, sending him back to the school, Edward changes his mind because he believes Ricky can teach him how to be a grown-up, as much as he can show Ricky how to be a kid. Written by Attmay

Ricky is pleased that Edward lets him get away with everything - until Derek tells him it means he doesn't care about Ricky. Edward has to show Ricky that his relaxed attitude toward discipline doesn't mean that he doesn't love him.

Ricky wants to meet his grandfather, but finds that Edward has no interest in seeing his father - an attitude that is definitely mutual. Knowing how important it was for him to know his father, Ricky devises a plan to reconcile the two.

Ricky insists on going to a public school so he can be more of a regular kid, but sticks out for being rich and gets a black eye from the school bully. Determined to not let Ricky get hurt, Edward hires Mr. T as his bodyguard.

Ricky gets his first taste of puppy love when a new girl transfers to his school. He also probes Edward about his romantic interests, just as Kate leaves for a singles cruise.

Evelyn, Edward's ex-wife and Ricky's mother, shows up and wants to take Ricky back to live with her in London. Leonard tells Edward he could fight for custody, but warns him that a legal battle could get to Ricky.

Ricky's expertise in computers attracts the attention of Arnold Jackson, school reporter at P.S. 98 in New York City. Ricky impresses Arnold by hacking into a military computer system, but when Arnold publishes their discoveries in the school paper it attracts the attention of the FBI. Written by Attmay

While out with Derek on a late-night expedition to look for Bigfoot, Ricky captures and brings home an escaped orangutan that he wants to keep as a pet.

Ricky saves his grandfather from embarrassment when his dad Edward refuses to speak at a banquet and present an award to his father.

Ricky convinces Edward to cancel his skiing trip and take him camping so that he can advance to the next level in scouting. However, the trip turns out to be a complete disaster.

Based on Derek's advice and a misunderstood conversation, Ricky is convinced Kate has fallen in love with him. Determined to find someone else for her, he decides to play matchmaker between her and his father.

Despite the previous night's kiss, Edward and Kate start to feel defensive about their romance. When they both arrange grudge dates to make each other jealous, Ricky schemes to have his father crash Kate's date at Carnegie Hall.

Edward and Ricky spend their first Christmas together, and after meeting a young boy from a family in a difficult situation, they decide to play Santa.

After Derek saves Ricky's life, he pressures Ricky to find him a date for a co-ed party. But when Ricky can't find any girls who are willing, he feels obliged to pose as Derek's date.

After Ricky gets in a fight with Ox, he and Edward are sued for a false whiplash claim. Leonard and Ricky convince the judge that the case be presented to a jury of peers - other kids.

Edward wants to hire a 12-year-old girl as a toy consultant, but she'll only take the job on one condition - that Ricky become her boyfriend.

When his school orchestra needs to raise money for a trip to Washington, D.C., Ricky commits Edward to buying 1000 bags of popcorn, without his approval or knowledge - but when Edward declines, Ricky has to sell the popcorn at the mall.

For a school business club assignment, Edward lets Ricky manage an ice cream parlor for a week, but Ricky discovers that running a business is harder than he expected.

Ricky is miffed when Kate joins his ski trip with Edward, and starts to worry that he'll increasingly be ignored as their relationship develops.

Grandfather Stratton offers Kate an executive position in California, hoping that Edward will marry an heiress to expand the family fortune. When Kate finds out, Edward's relationships with both her and his father seem to be over.

An old suitor of Kate's accidentally crashes his small plane on the grounds of the Strattons' estate, after flying low over the house in an effort to impress her, and Edward reluctantly invites him to stay due to his injured leg.