Anna Sale wants you to have conversation. You know the one. The one that you’ve been avoiding or putting off, maybe for years. The one that you’ve thought “they’ll never understand” or “do I really want to bring up?” or “it’s not going to go well, so why even try?” Sale is the founder and host of WNYC’s popular, award-winning podcast or as the dubbed her “a therapist at happy hour.” She and her guests have direct and thought-provoking conversations, discussing topics that most of us are too squeamish, polite, or nervous to bring up. But Sale argues that we all experience these hard things, and by not talking to one another, we cut ourselves off, leading us to feel isolated and disconnected from people who can help us most. In , Sale uses the best of what she’s learned from her podcast to reveal that when we dare to talk about hard things, we learn about ourselves, others, and the world that we make together. Diving into five of the most fraught conversation topics—death, sex, money, family, and identity—she moves between memoir, fascinating snapshots of a variety of Americans opening up about their lives, and expert opinions to show why having tough conversations is important and how to do them in a thoughtful and generous way. She uncovers that listening may be the most important part of a tough conversation, that the end goal should be understanding without the pressure of reconciliation, and that there are some things that words can’t fix (and why that’s actually okay).