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 tries to impress a student reporter by hacking into a secret military computer site, but the FBI closes in after the material ends up in the school newspaper. The boys decide their only way out is to hitch a ride on a tramp steamer.
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 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.
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.
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.
