Hopeless Books in Order

The Hopeless books follow a group of teenagers and young adults whose lives keep colliding around one central question, how much truth you can uncover about your past and still find a way forward. The tone is emotional and heavy at times, but the series always pushes toward healing.

It begins in Hopeless with Sky Davis, a girl who has been homeschooled and cut off from most of the world. When she finally convinces her mom to let her attend a local high school, she meets Dean Holder, a boy whose anger, guilt, and intense interest in her feel both magnetic and frightening. Their relationship starts like a typical bad boy romance, then slowly turns into a mystery about Sky’s missing memories and the secrets surrounding both of their families.

Holder’s side of that story comes next in Losing Hope. Instead of retelling every scene beat for beat, the companion novel folds in his childhood, his sister’s death, and the promise that has haunted him for years. Reading it after Hopeless fills in emotional gaps, especially around why he recognizes Sky and why he is so determined not to fail her again.

The tone lightens in Finding Cinderella, a novella that shifts focus to Daniel, Holder’s best friend, and Six, Sky’s irreverent neighbor and confidante. What starts as an almost mythical meeting in a dark closet turns into a search for the girl he calls his Cinderella, threaded with the same mix of humor and heartbreak that runs through the main novels.

All Your Perfects feels separate at first, following Quinn and Graham through the cracks in a once ideal marriage. Infertility, unspoken resentment, and the weight of old promises make their story quieter and more adult than the high school drama of the earlier books. By the end, though, its focus on how love survives disappointment fits neatly beside the rest of the Hopeless arc.

The final novella, Finding Perfect, pulls everyone into the same room. Set around a Friendsgiving dinner, it uses a simple gathering to revisit Sky, Holder, Daniel, Six, Quinn, and Graham, tying off loose threads from both the original trilogy and All Your Perfects. It reads like a long epilogue that lets readers sit with these characters after the worst of their trauma has been named.

If you are new to the series and want the emotional arc to build naturally, a common reading order is Hopeless → Losing Hope → Finding Cinderella → All Your Perfects → Finding Perfect. Expect serious subject matter involving abuse, grief, and mental health, but also a steady through line of friendship, found family, and the idea that knowing the truth, as painful as it is, can be the first step toward feeling less hopeless.