The following version of this book was used to create the guide: Zigman, Laura. Separation Anxiety. A Novel: HarperCollins Publishers, 2020.

Judy begins carrying her dog, Charlotte, in a baby sling to help alleviate her loneliness. She feels distant from her thirteen-year-old son, Teddy, and her husband, Gary. Judy and Gary are technically separated, a secret they have been keeping for two years from Teddy. The whole family still lives together because it would be too expensive for Gary and Judy to live apart.

Judy writes for a freelance health and wellness website, but she longs to return to writing novels. She spends her days picking up Teddy from school and waiting for Gary to return from work.

When Judy meets Teddy's teachers, she is embarrassed to bring Charlotte, but she feels as though she needs the emotional crutch of having the dog nearby. She and Gary attempt to go to therapy again. They leave early as always, convinced that there is nothing that can solve their deep-seated problems.

Judy begins to follow Sari, a creative life coach, and dreams of going to one of her retreats. In the meantime, Judy and Gary decide to host People Puppets, traveling puppeteers who will be performing at Teddy's school. By hosting, the couple hopes to get a tuition break.

Gary reveals to Judy that he kissed a woman he met at work. Judy does not react well to his news despite their agreement that they are both allowed to see other people. Due to Teddy's questioning, they must also begin sleeping in the same bedroom again. Judy resents how much space there seems to be between herself and Gary, but she does not know how to bridge the gap.

Judy decides to attend one of Sari's retreats in Vermont to try and get her own creativity back. She originally planned to take the short road trip with Teddy, but he does not want to go. Gary offers to go with her. They make the trip together, and Gary enjoys the creative aspect of the workshop. He used to be a musician, and he has always wanted to find the courage to overcome his anxiety and get back on stage. They return home without addressing the many issues that still exist in their marriage.

Judy's friend, Glenn, has been slowly dying of breast cancer. Judy attempts to prepare herself for Glenn's passing by clinging to Charlotte to give her the strength to do so. In the meantime, she arranges for Teddy to get braces.

When Judy and Gary go to Teddy's performance at school, they finally hash out some of their issues, but Gary does not want to move out and ask Judy for a divorce. The People Puppets, Nick and Phoebe, perform a skit depicting Judy and Charlotte and how much of a positive impact Charlotte has made on Judy's mental health. Gary has always believed that Judy intentionally tries to be disruptive or embarrassing with the baby sling. However, after he begins to understand the emotional roadblocks Judy has put up, they make some progress on their marriage. The family begins to heal from Glenn's death.