Isadora Wing Books in Order

The Isadora Wing novels follow one woman over several decades as she tries to work out what freedom really means. Across Fear of Flying, How to Save Your Own Life, and Parachutes & Kisses, Isadora moves from anxious newlywed to famous author to divorced single mother, always talking to the reader as if to a sharp, skeptical friend.

In Fear of Flying she is twenty nine, a poet who flies to a psychoanalysts’ conference in Vienna with her second husband, Bennett. She is terrified of planes and equally afraid of giving up the safety of marriage, yet bored by the role she is supposed to play. When she meets Adrian, an attractive British analyst who promises adventure, she runs off with him on a ramshackle car trip through Europe. The novel is less about their affair than about the furious, funny monologue in Isadora’s head as she weighs fantasy against the messy reality of love, family, and her own past.

Isadora is funny, self sabotaging, and painfully self aware, which is a big part of why readers still recognize themselves in her.

How to Save Your Own Life picks up a few years later. Isadora is now the author of a notorious bestseller and suddenly finds herself rich and in demand. Her marriage is crumbling, Hollywood comes calling, and the open marriages and encounter groups of 1970s California tempt her with new versions of liberation. The book follows the slow unravelling of a relationship and asks what kind of risks a woman will take in order not to feel trapped again.

By Parachutes & Kisses the world has moved into the 1980s and so has Isadora. She is divorced, sharing custody of a young daughter, and trying to raise a child while keeping her writing career alive. There is an ex husband to negotiate with, a big house in Connecticut that may or may not feel like home, and a parade of often ridiculous suitors. The comedy of dating as a nearly forty year old single mother sits alongside serious questions about money, caretaking, and what “having it all” really costs.

Read together, the books trace one consciousness aging in real time. The tone stays conversational and explicit about sex, but the stakes shift from whether to leave a husband to how to balance lovers, work, and parenting without losing herself. Jewish identity, psychoanalysis, and travel remain strong threads, as do Jong’s riffs on other books and writers.

Readers coming to the series now should expect long interior monologues, plenty of therapy talk, and more cultural name checking than most contemporary novels, all used in the service of charting how one woman thinks. The trilogy stands on its own, but Isadora’s later cameo as a wise, older friend in Fear of Dying shows how strongly she continues to live in Jong’s imagination and in that of her readers.