At its best, I’ll Have What She’s Having will remind readers of the humorous moments in Chelsea’s earlier books. During the COVID epidemic, she and several relatives spent part of the summer in a rental house in Maine. The trip included a memorable visit to former President Bush’s compound in Kennebunkport and a non-political meeting with the ex-president. Earlier, she describes moving to California as a 19-year-old. Her brother arranged for a traveling companion (whom she calls “Dipsy Doodle”) whose first question was whether they should stop in Harlem to get cocaine for the ride. Needless to say, the trip didn’t go well from there. Another comic highlight describes the fallout from an interview Chelsea gave with Andy Cohen in which she mentioned a threesome involving her former boyfriend, broadcasting executive Ted Harbert, and a masseuse.

Despite the humorous moments in I’ll Have What She’s Having, Chelsea also includes many serious ones. She does not pull punches and lays out her emotions. She goes into detail about her romance with the comic Jo Koy and their eventual breakup. However, the best essays in the book describe Chelsea’s relationship with the three daughters of a former boyfriend. Because both the boyfriend and his ex-wife traveled extensively, Chelsea wound up caring for the three girls, whom she dubbed Poopsie, Whoopsie, and Oopsie, a lot. As time passed, they even called her “Father,” because they viewed her as a friendly stepfather who would take the place of their absent father. Even after Chelsea broke up with their father, she remained in touch with them, apparently until now. The essays that describe Chelsea’s relationship with the girls are especially touching, and readers will recognize that she came to view them as the children she never had.

At its best, I’ll Have What She’s Having is funny and touching at times. However, much of the book is laden with descriptions of how Chelsea handled difficult moments, some of them trivial. An encounter in which a passerby berates her for not putting money in a parking meter turns into a conversation in which she pleasantly berates him for his attitude. She even notes he seemed young enough that with the “right direction,” his attitude could improve. I would have left a long time before this man did and chalked the whole incident up to another kooky celebrity. However, Chelsea felt this man was worth the time she spent trying to adjust his attitude and, later, the time she spent writing about him in this book.

While the parking meter incident may have been the most annoying essay in I’ll Have What She’s Having, others seemed merely pointless. One essay entitled “My Man” describes what she hopes for in an ideal man. (“Please bring me someone who can teach me things.”) This reads like something a middle school girl would write in her diary about qualities in her future husband, not a woman in her 40s. In another essay, she writes, “My middle name is Joy, and I now understand that joy is my purpose in life… Once I identified my purpose, my bright bulb and effulgence began to shine.” I didn’t find passages like this especially shiny.

While I appreciate Chelsea Handler’s desire to impart some life wisdom to readers, she chose an unsuitable vehicle. Instead of organizing her material by topics and presenting her thoughts in an organized fashion, Chelsea’s writing is scattershot. Valid, insightful observations are mixed with sophomoric aphorisms. As a self-help guide, I’ll Have What She’s Having is a mess. Fortunately, Chelsea combined this material with some of her usual wit and frank biographical material. That material is entertaining and, sometimes, insightful. Chelsea Handler’s latest book merits a marginal recommendation, but readers won’t be having the Chelsea they’ve enjoyed in her previous works.

NOTE: The publisher graciously provided me with a copy of this book through NetGalley. However, the decision to review the book and the contents of this review are entirely my own.