16 Books to Read After a Breakup, in the Order You Can Handle Them

For a couple of years Strayed wrote an anonymous advice column called Dear Sugar, answering strangers who were at the worst part of something. This collects the letters and her replies. The format is what makes it a week one book: two or three pages a piece, so you can read one while the kettle boils and stop without losing anything. She never tells anybody to be strong. She tells them the truth, at length, and then stays in the room with them instead of ending on a neat line.

Behrendt wrote this with Amiira Ruotola-Behrendt as a survival manual for the first sixty days, and it is aimed squarely at the part of you that keeps drafting messages you will regret. It is bossy, jokey, and occasionally very 2005 in what it assumes about men and women. It is also useful in a way the gentler books are not, because it hands you rules to follow at a time when your own judgment is demonstrably not working. Treat it as a friend who takes your phone, not as literature.

Winch makes one argument and makes it well: we file heartbreak under emotional and then feel mad when it behaves like something physical. He writes about the loops, the idealising of a person you were unhappy with a month ago, the hunt for a reason that will settle everything, and why the standard advice to stay busy misses what is happening. It is a TED book, 124 pages, no padding anywhere. You can read it on a bad Tuesday and wake up with a slightly better map of yourself.

Williams is a science journalist, so when her marriage ended she did the thing she knew how to do and turned herself into the subject. The book follows her through tests, odd experiments and conversations with researchers who study what separation does to a nervous system, with the personal story running underneath all of it. She tries several of the standard prescriptions for grief and reports honestly on the ones that did nothing for her. It is memoir and reporting at once, and it never once tells you that time heals.

Levine and Rachel Heller take attachment research and turn it into something usable: broad patterns in how people behave when they get close to somebody, anxious, avoidant and secure, and what happens when those patterns collide. The value is not in collecting a label for yourself. It is in seeing a dynamic you thought was unique to the two of you described flatly in research that predates your relationship by decades. There is a questionnaire, and it is not a magazine quiz. The examples repeat, deliberately.

Ephron wrote this out of the end of her own marriage, and it is the best case I know for the idea that comedy is what heartbreak becomes once you can stand up again. Rachel narrates her own collapse with jokes so good you keep forgetting how bad the situation is. There are recipes in it, actual recipes, because Rachel writes about food and cooking is what she has instead of composure. It runs 137 pages in the edition I checked and it wastes none of them.

Rob is in his mid thirties, runs a failing record shop in London, makes lists about everything, and has just been left. He goes back through his worst breakups hunting for evidence that none of it was his fault, and the novel lets him hunt while letting you see what he cannot. It is very funny about music snobbery and unusually precise about the ways men avoid saying the true thing out loud. If you are a man reading this list, this is the uncomfortable one, and it works best while it still stings.

Strayed was in her twenties, her mother had died, her marriage had ended and she was doing damage to herself in several directions at once, so she bought a rucksack she could barely lift and set off along the Pacific Crest Trail on her own. The book moves between the walk, which is brutal and frequently absurd, and the years that sent her there. What lifts it above the genre is that she does not arrive anywhere improved in a way you could put on a poster. She keeps walking until something settles.

Eleanor has a job, a flat, a weekend routine involving a great deal of vodka, and a way of speaking that makes strangers move away from her at parties. She is also, by her own account, completely fine. The novel is very funny for a long stretch and then quietly stops being funny, and the turn is handled well enough that you do not see it coming. It sits here because it is a book about loneliness that ends with human beings being useful to each other, which is the specific thing week six needs.

This is not a breakup book at all, which is precisely why it works. Gilbert writes about creative work: doing it without demanding that it justify itself, keeping it separate from your need to be praised, and why the fear that you have started too late is nearly always wrong. It is chatty and goes a bit mystical in places, and if that irritates you, skip those chapters and keep the practical spine, which is about making things badly and often until they get better.

Ansari worked on this with the sociologist Eric Klinenberg, and the result is a researched book with jokes rather than a joke book with a research chapter. There is a section on the psychology of waiting for a reply that will describe your last fortnight with unpleasant accuracy. There is a longer look at how our grandparents chose partners, mostly from a very small pool very close to home, which puts the anxieties of the apps in useful perspective. The app examples are from 2015 and dated. The behaviour underneath them is not.

Don Tillman is precise, literal, and baffled by other people, so he approaches finding a partner as a screening problem and builds a questionnaire long enough to frighten a statistician. Rosie fails nearly all of it, and the book is what happens next. It is a romantic comedy that runs on structure rather than sentiment, so it never turns gooey, and it is one of the few genuinely funny novels where the joke is never cruel to its own narrator. Quick, light, and it will not remind you of anything.

Rabih and Kirsten meet in Edinburgh, fall in love, marry, and then the book does the thing romance almost never does, which is stay. Arguments about the dishwasher. Resentment about who booked the holiday. An affair, and long ordinary stretches of boredom. Every few pages de Botton breaks in with an essay explaining the psychology under the scene, and the effect is like watching a film with a very clever friend who keeps pausing it. Whether that reads as helpful or intrusive will decide how you feel about the whole book.

Lunn spent years asking people who think seriously about love the questions she could not answer herself, and the book is built in three parts: how we find it, how we sustain it, how we survive losing it. The interviews sit next to her own story, which includes long stretches of not having the thing she wanted while writing about people who did. It is a gentle book without being a soft one, and the final third contains the best writing about loss anywhere on this list.

Toru is a student in Tokyo at the end of the sixties, in love with Naoko, who is carrying a loss the two of them cannot talk about properly, and pulled at the same time towards Midori, who is alive in a way Naoko cannot manage. Murakami keeps it realist here, no talking cats, no parallel worlds, and what remains is a novel about grief moving through young people who have no vocabulary for it. It is beautiful and heavy, and the ending refuses to console you.

After a divorce that flattened her, Gilbert spent a year across Italy, India and Indonesia, eating, praying and eventually falling in love again. The Italy section is genuinely good, funny and specific about pleasure as a discipline rather than a reward. The India section, set in an ashram, is the one Indian readers will find strangest, for reasons Gilbert did not intend. The Indonesia section is where a lot of readers quietly stop. The writing stays warm throughout, and the shape of the whole thing rests on a book advance most of us will never see.