Below is the complete list of Colleen Hoover’s Hopeless books in order. For this series, the chronological reading order is the same as the order of publication.
Publication Order of Hopeless Books
About Hopeless
Colleen Hoover’s Hopeless series is a contemporary young adult and new adult romance sequence built around trauma, memory, love, and the painful process of uncovering buried truth. The series begins with Hopeless, the novel that introduced Sky Davis and Dean Holder, and later expands through companion perspectives and connected stories that deepen the emotional history around the main characters. It is one of Hoover’s most recognizable early series because it combines romance with mystery-like revelation, gradually reshaping what the reader understands about the characters’ pasts.
Hopeless centers on Sky, a teenage girl who has grown up with an unusually sheltered home life and little direct experience with the ordinary routines of school, technology, and social expectation. When she meets Holder, a boy with a reputation for intensity and unpredictability, she feels a strange pull that she cannot easily explain. Their relationship begins with attraction and suspicion, but the novel’s true structure depends on memory. Sky’s emotional reactions, Holder’s guarded behavior, and the gaps in what both characters know slowly point toward a past that is more painful and complicated than either can ignore.
Holder is central to the series because his role is not simply that of a brooding romantic lead. He carries grief, guilt, and knowledge that affects every choice he makes around Sky. Hoover uses his character to explore the burden of surviving loss and the danger of believing that love means carrying pain alone. In Losing Hope, the events of Hopeless are retold from Holder’s perspective, which changes the emotional emphasis of the story. The companion novel does not merely repeat the first book; it gives readers access to Holder’s private thoughts, his relationship with his sister Les, and the emotional weight behind actions that Sky could only interpret from the outside.
The shorter work Finding Cinderella shifts attention to Daniel and Six, characters connected to the Hopeless world. Their story has a lighter surface, with a more playful and unexpected romantic setup, but it still carries Hoover’s interest in secrets, vulnerability, and the fear of being truly known. All Your Perfects later connects to the series through Daniel and Six’s wider circle, while Finding Perfect serves as an important bridge that brings emotional closure to threads involving the connected characters. Because of these companion links, the Hopeless series can feel broader than a simple two-book Sky and Holder story.
The series is emotionally intense and deals with difficult subject matter, but its central concern is not shock. Hoover is interested in how people survive what they could not control, how memory protects and harms, and how love can become part of healing when it is rooted in honesty rather than rescue fantasy. Sky and Holder’s relationship is powerful because it forces the truth into the open, even when that truth threatens the fragile stability they have built.
Hopeless is best understood as a connected emotional-romance series rather than a traditional plot-driven saga. Its books and companion stories circle around the same themes from different angles: lost innocence, grief, secrecy, trust, and the possibility of building a future after the past is finally named. The series remains one of Hoover’s defining works because it shows her early ability to combine romance, suspenseful revelation, and raw emotional consequence in a way that feels intimate and deeply personal.