Punky and Cherie send Henry on a blind date with Ms. Maytag, the school librarian, then they talk Betty into appearing on the TV show "Dream Date", where out of the three women on the show, overweight contestant Chuck McKinley chooses Betty.

Punky's friendship with Cherie is put to the test when Cherie falls for Donald Sotta, a new boy in the neighborhood, and Cherie begins to spend more time with Donald than she does with Punky, making a jealous Punky think Cherie likes Donald more than she likes Punky, until Cherie proves Punky wrong by telling Punky that Cherie loves Punky as her best friend, and Cherie doesn't like Donald so much anymore because all Donald cares about is baseball, basketball, and wrestling.

In a special episode: Allen is scared to death that his parents Andy and Annie are going to get a divorce because Andy and Annie have been arguing a lot lately, more than usual. It turns out that Allen is right, and Andy and Annie decide to get a divorce. Later, Punky finds Allen in the treehouse with a lot of his things. Allen says he's never leaving the treehouse, and Punky is shocked by the reason why -- Allen has to move to Kansas with Annie. Allen doesn't want to leave his friends and move to an unfamiliar place. Henry comes outside and tells Allen that Annie is looking for him. Punky and the gang say a tearful goodbye to Allen, and Punky tells Allen that she and the gang will always be Allen's friends, and that they will always stay in touch with Allen.

Punky tells Henry that she is afraid of being in any vehicle driven by her friend Joey Deaton's father Mike Deaton, because Mike has a drinking problem, but Joey and Henry are reluctant to believe Punky, even though she's telling the truth. When Henry and Joey see for themselves what Punky saw, they apologize for not believing Punky, and Mike decides to get help for his drinking problem.

A stubborn Joey thinks he should keep Brandon, while his mother thinks he should do the right thing and give Brandon back to Punky, but Brandon escapes from Joey and shows up at Punky and Henry's door, being chased by Joey and his mother.

Henry tries to overcome his fear of public speaking when he helps Punky petition city council to turn a vacant lot into a park -- but another man, Mr. Arnold, wants to put a mall in the lot, not realizing that Chicago has too many malls already. Henry does speak for Punky in front of the city council, and the city council decides to turn the vacant lot into a park.

When Henry's most valuable employee, Stanley, quits his job, Henry tries to find a replacement for Stanley, but to no avail. Punky tells Henry that she needs money to pay her own way into summer camp, so Henry hires Punky, then promptly fires Punky for wrecking havoc in the restaurant, starting a feud between Punky and Henry. Henry believes Punky should have taken the time to learn how to do some of the things that she made mistakes doing, while Punky just wanted to do a good job for Henry.

After discovering that Henry has become addicted to the sleeping pills that were prescribed for him six months ago when back pain kept him awake at night, Punky helps Henry realize that he has an addiction, and she helps him make the decision to stop taking the pills, because he doesn't need the pills anymore, and Punky wants him to be around for a long time.

Punky decides that she would rather go on a yacht on Lake Michigan with Cherie and Margaux rather than stay home and take care of Brandon, until she has a dream that shows her how it feels to be Brandon.

Punky is invited to the birthday party of rich kid Robert Whitney when Henry is hired to be the party's photographer. In order to keep from embarrassing Henry, Punky takes lessons from Margaux on how to act like a rich stiff. The lessons don't work -- Punky ends up wreaking havoc and has Robert wishing that his social secretary Charles hadn't invited any stiffs to the party, because Robert didn't want the party to be as boring and stiff as Charles wanted it to be.

Punky decides to write a gossip column in the school newspaper, and she soon finds herself in hot water with her teacher, her schoolmates, and Henry when the gossip column does nothing but cause problems, especially when Punky's column tells her teacher, Mrs. Winston, which class put a frog in Mrs. Winston's briefcase. Mrs. Winston thought it was her biology class, but it was her history class.

Punky and Cherie enlist the help of the other tenants to help keep Maude Firestein from having to move to a nursing home. Maude is a favorite neighbor among the tenants, and the only tenant who doesn't like the effort to keep Maude from moving is chronic complainer Pete "The Crank" Frank. With a lot support from the neighbors, it turns out that Maude doesn't have to move.

Brandon runs away, and while Punky and the gang spend six hours searching for Brandon, Joey Deaton, a kid Punky's age, takes Brandon in, and hopes Brandon can move to California with him and his parents.

A blizzard traps Punky, Henry, Betty, Cherie, Margaux, and Brandon in Henry and Punky's apartment, where the gang passes the time by remembering past situations that they've been in, with flashbacks to past episodes.

After learning that Punky did not do her book report, Henry cancels Punky's plans to see her favorite singing group DeBarge in concert, a move that Punky vows to never forgive Henry for -- until Henry gets DeBarge to come to the apartment and tell Punky how important reading is.

When it's time for Punky to get her first bra, Henry is the one who has the growing pains, because he finds it hard to accept that Punky is growing up.

Punky befriends a pig at the mall, and she kidnaps it when she discovers that its owner, Jimmy John, plans to have it butchered, but Henry tells Punky that she must return the Pig to Jimmy John, who decides not to have the pig butchered. He decides to feature the pig in an ad campaign.

In a saddening episode: Henry has bought tickets to the circus which is scheduled for the next day, May 9th. When Cherie starts acting strange and says she can't go to the circus, Punky remembers that Punky's diary says that Cherie acted the same way on May 9th of last year too. Punky wants to know why Cherie likes to be alone on May 9th of every year, so Punky decides to follow Cherie around on May 9th -- and discovers that May 9th is the anniversary of the day Cherie's parents, Ronald George Johnson and Elizabeth Marie Johnson, died in a car accident in 1981, and Cherie is still having problems coping with the tragedy, because she feels guilty, thinking that the accident was her fault because her parents were on their way to pick her up from school. Punky talks to Betty, who says that Cherie never talks about her parents, not even to Betty. Cherie has never even been to the cemetery where Ronald and Elizabeth were buried. Cherie has kept her feelings about the deaths all balled up in

While Henry is closing his studio for the day, he is approached by Matt Glossy, the owner of Glossy's, which is a multi-million dollar empire of photography stores. Glossy admits that his real name is Sam Glossy, and that the name "Matt Glossy" sounded better to use for business. Glossy wants to open a new branch of Glossy's in the mall that Henry's studio is in, and Glossy thinks Henry's studio is in the spot Glossy is looking for, so Glossy offers to buy Henry's studio for $100,000 so he can turn it into a branch of Glossy's. Henry accepts the offer and Glossy hires Henry as the manager of this branch of Glossy's. Henry, who has been a photographer for 43 years, feels so miserable working as the manager that he ends up quitting. Punky convinces Henry to take some of the $100,000 he got from Glossy and open up a new restaurant. Since it was Punky's idea, Henry names the new restaurant "Punky's Place".

Overweight classmate Farley "Spud" Blugner has a crush on Punky, but rejection from Punky sends him out on the window ledge on the 6th floor of the apartment building Spud lives in, when Punky refuses to ask Spud to the Sadie Hawkins Day dance.

Punky and Henry get a visit from Henry's overweight niece Louise. After Louise is insulted by Margaux, Louise says that she's unhappy with her weight, so Punky helps Louise go on a diet.

Punky fakes being sick so she can avoid school and can go to the movie theater to see "Slime Wars In Space" -- an R rated movie that Margaux and Cherie have each seen twice, and Punky feels left out because she hasn't seen it at all. Punky does end up seeing the movie.