Bobby does not want to stay at Aunt Ruth's house. He thinks he'll be bored and she smells. However, Bobby finds that being with his Aunt Ruth is actually fun and he begins to look forward to going over again.

Uncle Ted and Bobby decide to have a campout in the back yard. This is Bobby's first time sleeping outside and he does not know if he is ready. At first Bobby can't wait, but when he finally does campout with Uncle Ted he is frightened by many things.

Bobby's parents and Kelly are going out. Bobby and Derek are upset because they are getting a babysitter, but things turn out better than they thought.

Bobby goes with his family to the mall, but ends up getting lost.

Bobby's dad tries to fix a plumbing problem in the house... with not much luck.

Bobby shows Roger his leash and he runs away. Now everyone has to find Roger.

Bobby loses one of his mom's irreplaceable bedroom slippers.

It's Halloween and Bobby is too little to go trick or treating, so Uncle Ted helps Bobby turn the house into a Halloween House of Horror.

Uncle Ted takes the family out on his new boat and they end up stranded on an uncharted island.

Bobby is afraid to see a new doctor after watching a scary movie on television.

Bobby goes with his family to a relative's wedding, having the dubious distinction of ring bearer. There are of course mishapps on the way to the wedding.

The family goes on a road trip to the Grand Canyon. Unfortunately, the trip doesn't go as smoothly as Howie thought it would.

Uncle Ted takes Bobby to a museum while Bobby daydreams about cartoons.

The Generic Family finds out that Martha's pregnant.

Bobby accidentally crushes his mother's prized Elvis bust, but tries everything he can to pretend it never happened.

Bobby invites his friends to join his new club. However, when he forbids someone from joining, his parents move in.

Bobby watches a scary movie at the drive-in theater and has nightmares until Uncle Ted tries to help.

Bobby spends a day at work with Howard at his office.

Bobby has his first day at pre-school.

Bobby competes in a neighborhood olympics. Things turn sour when his family starts putting too much pressure on him to win.

Bobby's fifth birthday was put off by Martha going into labor, only to realize it is a false alarm. The rest of Bobby's family work to make his makeup party a success.