Then Again, Maybe I Won't

Twelve-year-old Tony Miglione lives with his hardworking extended family in a working-class neighborhood in Jersey City, New Jersey. After Tony's family experiences a major increase in wealth due to his father's successful sale of his electronics invention, the family relocates to an upper-class community in Rosemont, New York. His mother becomes absorbed with climbing the social ladder in her new, wealthier neighborhood, while his maternal grandmother becomes angry and withdrawn when she is no longer allowed to cook for the family as she loves to do. Tony's older brother, a new father who was previously a well-respected junior high school teacher, gives up teaching to make more money working for Tony's father, causing Tony to feel that his brother is "selling out".

Tony meets a seemingly polite and respectful neighbor, a boy his own age, Joel Hoober. While Joel's manners impress Mr. and Mrs. Miglione, Tony sees Joel's true colors in private. Joel secretly engages in misbehavior such as prank calls, underage drinking, hiding issues of Playboy magazine under his bed, and shoplifting, and encourages Tony to participate as well. Tony starts to experience inexplicable abdominal pain brought on by his anxiety over his new friend's antics. Tony also develops an infatuation with Joel's beautiful teenage sister Lisa, who routinely undresses near her uncovered bedroom window, as Tony watches from his own bedroom window. He is going through puberty and must deal with the physical changes in his body, such as wet dreams and erections, on top of the major changes in his family life. It is implied that he masturbates and thinks of Lisa when he does it.

After witnessing one of Joel's misdeeds, Tony faints from anxiety, where he is then admitted to the hospital for a brief stay and sent to therapy after doctors determine the malady is not medical. The therapy helps Tony learn new ways to cope with his problems. Joel is eventually caught stealing golf balls from a sports store, and Tony refuses to stand up for him when they are stopped by security. Surprisingly, Joel isn't angry at him and the two boys agree amicably to end their friendship, and Joel is sent to a military academy after explaining to Tony that he acted out to see if he could get away with it. When Joel's mother rationalizes his behavior by announcing the forthcoming enrollment in the military academy, Tony's mother is considering sending him there too, until Tony's father intervenes and says this is a key decision that only Tony should make. Tony regains some respect for his parents after realizing they do pay attention to him, unlike the Hoober parents towards Joel. Tony also overcomes his infatuation with Lisa and curtails watching her window after learning of her relationship with his youth group leader. At the final chapter, Tony is bicycling and talking to himself about his parents building a swimming pool and he is approaching his 14th birthday. Tony is also now more at ease with himself and the family changes, and had the courage to tell the therapist he spied on Lisa. Tony thinks it would be best if he cuts it out with his Peeping Tom behavior for good, but finally says to himself "Then again, maybe I won't".

• Anthony (Tony) Miglione – Protagonist of the book who is 12 years old, the youngest of three boys.
• Victor (Vic) Miglione – Tony's father, who is a freelance electrician and an inventor whose invention changes their life.
• Carmella Miglione – Tony's mother, who eventually goes by the name Carol, much to Tony's dismay.
• Ralph Miglione – Tony's older brother who is a teacher at his middle school in Jersey City, NJ, but goes into the family business with his dad, which angers Tony to no end. Back in Jersey City, Ralph was respected amongst Tony's peers, known as "The Wizard of Seventh Grade Social Studies".
• Grandma – Carmella's mom, who cannot speak after having her larynx removed due to cancer. She loves to cook, but was no longer permitted to do so after hiring their housekeeper, so she spends every day in her bedroom watching TV, depressed.
• Vincent (Vinnie) Miglione – Tony's deceased older brother. He died in Vietnam a few years before the story takes place.
• Angie Miglione – Tony's sister-in-law, and Ralph's wife.
• Vincenza (Vickie) Miglione – Tony's niece, and Angie and Ralph's daughter. She was named after Vinnie.
• Joel Hoober – Tony's new friend in Rosemont. He's a practical joker and a shoplifter.
• Marty Endo – One of Tony's new friends who is also one of his basketball teammates and a member of the church youth group.
• Scott Gold – Another new friend of Tony’s, who is in all of Tony's classes at school. He is often seen with Tony, Marty Endo, and Joel Hoober as a group.
• Lisa Hoober – Joel's attractive 16-year-old sister, who Tony develops a crush on, and spies on with binoculars via his window
• Kathryn (Corky) Thomas – A girl Tony’s age who likes him, but he pays her little attention.
• J.W. Fullerbach – Vic's new boss and partner.
• Frankie Bollino – Tony’s best friend from Jersey City who comes to visit him.
• Dr. Fogel – Tony's psychiatrist.
• Maxine – Housekeeper to the Migliones who directs the house her way and won't let Tony's grandmother cook anymore.
• Millicent – Housekeeper to the Hoobers who seems to be the only one who is aware of Joel's antics because one night when Tony is at Joel's house she catches them in Lisa's room.

While this novel is similar to aspects of Are You There God? It's Me, Margaret., it differs mainly in the secondary themes. While Margaret struggles with her issues of religion and being raised in an interfaith family, Tony Miglione struggles with the issues of his family's social status and to a lesser extent, American society. A similarity of both stories, aside from the physical maturity of both characters, is that Tony develops a crush on the eldest daughter of his next door neighbors, just as Margaret has feelings for her neighbor's friend. However, Tony also has to deal with the fact that she is three years older than he is, and, that if such a crush developed further, the age difference would be uncommon among boys he knows. Both stories also deal with moving from an urban area to the suburbs, but the reason behind the move for Tony's family is his father's success with his invention and desire to move to a wealthier community.

Themes dealt with include the effects on Tony of losing the working-class life he had been used to in his Italian-American neighborhood in Jersey City, and being ill at ease in his new upper-class community. In addition, Tony's grandmother has been marginalized, as she loved to cook for the family in Jersey City but is told that this would be inappropriate in their new home. She confines herself to her room after the Migliones hire Maxine, a maid who takes advantage of the family's inexperience with their new lifestyle, and essentially directs the household to her taste instead of taking orders from the family.

Another slight theme touched upon is Tony regaining slight respect for the working class life his parents left behind. Tony and his friends are drinking milkshakes at a malt shop when Joel thinks it is cute to hide the tip inside a partially unconsumed milkshake glass, causing the waitress to make a scene and remark how Joel and his ilk know nothing of working for a living and that "your crummy coins buys me a loaf of bread; ever stop and think of that". Tony later remarks to himself he thought for a long time how his spending money goes from his pocket to a supermarket in some low-income neighborhood.

The penultimate chapter in the book deals with the consequences of Joel's immoral actions. Tony and Joel are at a sporting goods store where the employees successfully catch Joel shoplifting golf balls and Tony refuses to aid Joel in lying. Tony anticipates that his parents will learn for themselves of Joel's true nature when they read tomorrow's newspaper and see Joel will be remanded to the juvenile facility, but is surprised when he learns the owner of the sporting goods store declines to press charges against Joel for shoplifting. Joel's father then decides to enroll Joel in a military academy, which he believes will cure Joel of his "I will do what I want, when I want" attitude and deprive him of his pampered lifestyle at the Hoober home, but also shows Mr. Hoober pigeonholing the problem so his work and golf games are not interrupted.

The time frame of this story is evidently the late 1960s or early 1970s, as Tony's eldest brother, Vinnie, has been killed in action in the Vietnam War. Initially set in Jersey City, New Jersey, the family eventually moves to Rosemont, New York on Long Island. Other themes touched upon are how Tony's family seems to be knowingly and willingly distancing themselves from their Italian heritage as not many Italian-Americans live in Rosemont (evidence of this is shown when Tony's mother allows herself to be called "Carol" by Mrs. Hoober instead of Carmella, her true name). Another theme is how Tony's family is keeping up with the Joneses by emulating their next door neighbors, the Hoobers (although Tony's mother is clearly more concerned with social image than his father). Mr. Hoober is vice president of a pharmaceutical company and is apparently extremely well compensated, which gives his wife the chance to spend her days playing golf and socializing. The Hoobers are representative of the "high-powered American family" and seem to believe the "American way" is about money, affluent living, social status and not much else. As a result, they do not seem to give much attention to the trouble-making son Joel, who has the idea he can get away with anything because nobody is watching over him or enforcing discipline.

• ISBN 0-87888-035-6
• ISBN 0-8161-4417-6

• Judy Blume's website