Will starts sleeping in his own room, but gets scared of all the strange noises that occur. / Will wants to wear a pair of big-boy boots like his older brother Fred, but struggles to put them on.
Will gets dared by one of his classmates to drink a jar of pickle juice, meanwhile Dewitt gets dared by an old pen pal to perform a series of ridiculous antics. / With Dewitt's help, Will tries to make breakfast for Mom and Dad.
Will over-prepares a camping trip in the backyard for him and his friend Sam. / Will accidentally stains his new pair of pants.
With Mom busy, Will gets tasked to watch over his little sister Kate. / Will has to clean his messy room.
Will and Dewitt struggle to keep a secret. / Will gets to perform in the school play, but has trouble remembering his lines.
Will goes on a trading frenzy with his friends and classmates. / Will tries to come up with thank you cards for a bunch of gifts given to him for his birthday.
Will and Dewitt journey down the vents in their house to retrieve a toy Will accidentally drops down. / Mom and Dad hire a teenage babysitter to look after the kids, and Will's nervous.
When Will gets called “sir” at a restaurant, he tries to act more mature and quits his usual childish activities, including playing with Dewitt. / Will stays up past his bedtime in an attempt to watch a solar eclipse.
Will and Dewitt turn a simple walk to Sam's house into a life-threatening adventure. / Will plants potato seeds in the garden and can't wait for them to grow.
Will's finally tall enough to go on the fair's roller coaster, but struggles to work up the courage to ride it. / Will has to draw a self-portrait for the school's art gallery.
Will gets a new alarm clock that schedules his whole life. / Will becomes the ring bearer for his aunt's wedding.
Will tries to come up with a funny joke tell his friends at the school lunch table. / Will gets to choose where he and his family will go this weekend, but has trouble amidst pressure from everyone in the family.
Will tries to make a gift for Sam's birthday party. / Will and Dewitt go to the library.
After Fred shows off an amazing whistle, Will has a hard time trying to imitate it. / Will keeps forgetting to do everything and tries to come up with ways to remember.
Will watches over the class' pet python, who is accidentally let loose in the house. / During a game of baseball, Will knocks the ball into the backyard of his neighbor, who he's heard plenty of scary things about.
Will makes a bet with his friend Sandra for her tape-recording pen. He wins, but ends up feeling guilty about it. / Will doesn’t get an invitation to go to Sandra's birthday party and gets paranoid thinking he's done something for her to exclude him.
Will finds a lost walkie talkie and tries to find the original owner. / For a family trip to visit his grandma, Will goes on an airplane for the first time and gets nervous.
While Kate goes out shopping with Mom, Will borrows her doll for a game of his and ends up losing it. / After Will has a hard time practicing for his first baseball game, he instead tries relying on a series of weird and gross superstitions to help him win.
To prove he's responsible enough to own a pet, Will watches over his neighbor's dog. / Dad accidentally runs over Will's bike, and Will doesn't want to get a new one.
Will gets quarantined for chickenpox. In the meantime, he goes on a series of imaginary adventures to help Dewitt with his frog pox. / Will and Sam form a secret club in Sam's backyard shed.
When Will gets featured on the local newspaper, he starts acting like a huge celebrity and lets his newfound fame go to his head. / Will rallies his friends and family together to clean Dewitt's childhood creek.
Will watches over Sam's pet betta fish. / Will has to come up with an interesting report for the school's news program.
After a petty argument causes Will and Sam to break up as friends, Will tries to find himself a new one. / Will struggles to read his first book without any pictures.
When Will gets a gift certificate to spend at the toy store, he has a hard time deciding what to buy. / Will and his family are going to a foreign restaurant, and Will's reluctant to try out the new food being served there.
Will get a house key and struggles with the huge responsibility of trying not to lose it. / When Will has trouble learning how to skateboard, he comes up with his own method of skateboarding.
Will's substitute teacher informs his parents that Will might need glasses. / After Will messes up a compliment during an autograph with Frog Boy, he and Dewitt go on an adventure to the Grotto at the End of the World to find him.