Top Picks: Advice Columnists

When I think about why I love reading so much, the quote “We read to know we're not alone” (from William Nicholson's Shadowlands) always comes to mind first. Rarely does that line ring more true than when I relate to a story shared in an advice column. With the fresh start the new year offers, I'm drawn to a variety of advice columnists who encourage a new approach to the same old problems.

Many columnists are also authors, so if you like the way they give advice, try their books for more writing in the same style.

Let's start locally with Amy Dickinson's no-nonsense advice column Ask Amy, available via our online resource Chicago Tribune. In The Mighty Queens of Freeville: A Mother, A Daughter, and the People Who Raised Them, Dickinson describes how she weathered life's pitfalls with love and support from the "Mighty Queens" (her mother, aunts and sisters) in her tiny hometown in upstate New York.

The Dear Sugar podcast from bestselling writers Cheryl Strayed and Steve Almond tackles life's heaviest questions with the promise of radical empathy. The podcast grew out of Strayed's Dear Sugar column on TheRumpus.net (2010-2012); the best of these are collected in Tiny Beautiful Things, which showcases the depth of Strayed's compassion as she shares personal anecdotes and urges letter writers to hang on and work to make their lives better. If you've read the memoir Wild, you know Strayed possesses the life experience to understand our darkest places. The author of short stories and nonfiction, Almond's latest is Against Football: One Fan's Reluctant Manifesto. Part memoir, part reporting, the critique demonstrates he shares Strayed's willingness to challenge us.


Tiny Beautiful Things is available in other formats.

Wild is available in other formats.

Against Football is available in other formats.

Best known for his sometimes raunchy, sometimes snarky Savage Love column and Savage Lovecast, Dan Savage also writes essays and memoirs. He shares his journey to parenthood in The Kid, a frank and touching account of adoption by a gay couple in the 1990s, and later to marriage in The Commitment, which explores both the personal and the political of same-sex marriage.

The Kid is available in other formats.

The Commitment is available in other formats.

While Mallory Ortberg takes on tough topics in Slate's advice column Dear Prudence, her book, Texts From Jane Eyre, features fictional dramas. Ortberg imagines text exchanges from beloved literary characters, from the March girls to Scarlett O'Hara to Harry Potter, in this lively and fun book that's perfect for a break from any self-obsession these advice columns inspire.

Texts From Jane Eyre is available in other formats.