Dickinson was born and raised on a small dairy farm in Freeville, New York. She attended Clark University in Worcester, MA from 1977 to 1978 and transferred to Georgetown University. She married Anthony Mason, a CBS News correspondent, in 1986. They moved to London in 1987. A daughter, Emily, was born there in 1988. The couple divorced in 1990. Dickinson married Bruno Schickel, a builder from Dryden, New York, on August 16, 2008.
Dickinson has worked as a producer for NBC News. Her articles have appeared in such publications as The Washington Post, Esquire, and O. She wrote a column on family issues for Time, and produced a weekly column for AOL's News channels, drawing on her experiences as a single parent and member of a large, extended family.
In 2003, Dickinson succeeded Ann Landers (Esther Pauline "Eppie" Lederer) as the Chicago Tribune's signature advice columnist. Tribune Media Services syndicates Ask Amy to newspapers around the world.
Dickinson is a frequent panelist on the radio game show Wait Wait... Don't Tell Me! that is distributed by NPR, and was a regular featured guest on Talk of the Nation. She has also appeared on Car Talk with questions about how to respond to car problems in her column.
On February 9, 2009, Dickinson's memoir, The Mighty Queens of Freeville: A Mother, a Daughter, and the Town That Raised Them, was released by Hyperion Books. It reached The New York Times bestseller list in two weeks, debuting at number 16.
In November 2016, Dickinson announced the release of her second memoir, "Strangers Tend to Tell Me Things: A Memoir of Love, Loss, and Coming Home," coming in March 2017 from Hachette Books.
Homophobic letter and viral response
On Monday, November 18, 2013, Dickinson ran a letter from a parent who wanted his son to "stop being gay" because the parent found it embarrassing. It was signed "Feeling Betrayed." Dickinson responded:
Dear Betrayed: You could teach your son an important lesson by changing your own sexuality to show him how easy it is. Try it for the next year or so: Stop being a heterosexual to demonstrate to your son that a person’s sexuality is a matter of choice — to be dictated by one’s parents, the parents’ church and social pressure.
I assume that my suggestion will evoke a reaction that your sexuality is at the core of who you are. The same is true for your son. He has a right to be accepted by his parents for being exactly who he is.
The letter and response became a sensation after being posted on Upworthy and BuzzFeed and tweeted by George Takei.
In an interview with GoPride.com, an LGBTQ website, Dickinson addressed the letter's popularity:
I've been saying the same thing over and over and over again. What's interesting is that social media has changed the equation so much. I could probably find Q & As similar to this from years ago, but because there wasn't Twitter and Facebook and George Takei didn't have 5 million followers, it was just confined to people who read the newspaper. Now, oh my God, it's unbelievable. I actually heard from people who said that the letter wasn't real and that I planted that letter so it would go viral. My response is, 'If I could make something go viral, I would do every day.' It's in the very nature of virality, you can't make it happen.