Amy Dickinson pens the "Ask Amy" column for the Chicago Tribune, which is now syndicated in over 200 newspapers nationwide, including the Los Angeles Times, Newsday, the Seattle Times, the Boston Herald, the Baltimore Sun, the Charlotte Observer, the Orlando Sun Times, and the Philadelphia Enquirer. She joined the Tribune in July 2003 as the newspaper's signature general advice columnist, succeeding the legendary Ann Landers.

From 1999-2002, Dickinson wrote a column for TIME magazine focusing on family life and parenting, often drawing from her experiences as a single parent and member of a large, extended family. For the past ten years, her commentaries and radio stories have been featured on NPR’s All Things Considered. She also has provided commentary to CBS Sunday Morning.

Dickinson attended Clark University in Worcester, Massachusetts and graduated from Georgetown University in Washington, D.C. In the early days of the Internet, she wrote a weekly column for America Online's News Channel. She also has worked as a receptionist for The New Yorker, a producer for NBC News, a lounge singer, and a freelance writer. Her work has appeared in The New York Times, The Washington Post, Esquire, Allure, O magazine and other publications.

Dickinson hails from the Finger Lakes region of New York and is a distant relative of poet Emily Dickinson. Her large family has lived in and around her hometown (pop. 450) continuously since the Revolutionary War. She has described them as "hilarious, short-waisted Methodists."

"My extended family is a collection of married and divorced parents, single mothers, step-relatives, adoptees, devoted siblings, cousins, aunties, uncles, and grandparents. I grew up hearing stories about my ancestors’ exploits. My great grandfather was warden of Sing Sing Prison and my great uncle ran off to Europe and joined the circus when he was 40. Life in my hometown was like growing up in Lake Wobegon, only with worse weather and high unemployment," she says.

Dickinson has been a Sunday school teacher for ten years and is a substitute teacher at a local nursery school. She lives in Chicago with her teenage daughter.