Looking for friendship books that go past the usual advice? This collection has two halves: the classic essays that asked what a friend actually is, and the practical guides for making friends now.
Cicero wrote his treatise on friendship in 44 BC, and people still reach for it when a friendship ends. Montaigne, Emerson and Bacon each took a turn at the same question, and none of them agreed completely.
The practical half covers conversation, trust, and keeping a friendship alive once life gets busy. Every book is free to read online or download as PDF.
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Classics
Classic Essays on Friendship
The oldest books on friendship are still the sharpest. Cicero, Montaigne and Emerson were not writing self-help, they were working out what we owe the people we choose.
Cicero's two late essays, written in 44 BC, on growing old and on what actually binds friends together. His argument is that real friendship is only possible between people of good character, and that it cannot be bought or traded.
The complete essays in the Cotton translation, including Of Friendship, written after the death of Etienne de La Boetie. Montaigne insists the bond he is describing shows up perhaps once in three centuries.
Both series of Emerson's essays, including Friendship, where he treats a friend as a paradox: someone you need badly and must still leave completely free. Clean modern typeset edition.
Bacon's collected essays, with Of Friendship arguing that talking things through with a friend is the only real relief for a crowded mind. The volume also carries New Atlantis and long pieces by Milton and Browne.
Books eight and nine hold the oldest sustained analysis of friendship in Western philosophy. Aristotle sorts friendship into three kinds, built on usefulness, pleasure, or character, and argues only the last one survives.
Making friends as an adult is a skill, and these books about making friends treat it as one. Expect exercises on starting conversations, following up, and repairing a friendship after a long silence.
Seven communication skills turned into exercises you can practice: listening more carefully, saying what you mean, asking instead of assuming, and thanking people properly. Written for work, family and friendship alike.
A full university course on relationships with an entire chapter devoted to friendship: how friendships start, the stages they pass through, and what makes them end. Comes with exercises and review questions.
What happens to friendship when most of it runs through a screen. Petricini follows the idea from Aristotle to social media and asks whether contact at a distance can carry the same weight as the real thing.
An introduction to communication studies covering listening, verbal and nonverbal signals, perception and conflict. Solid groundwork if conversation feels harder than it should.