Dickinson has appeared as a social commentator on ABC's Good Morning America and NBC's The Today Show.

In 2003, Dickinson succeeded Ann Landers (Esther Pauline "Eppie" Lederer) as the Chicago Tribune's signature advice columnist.

[5] Tribune Content Agency[6] syndicated Ask Amy to newspapers around the world.

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.

On May 24, 2024, Dickinson announced her retirement from writing the "Ask Amy" column, with its final installment to be published at the end of June 2024.

Dickinson responded: Dear Betrayed: You could teach your son an important lesson by changing your own sexuality to show him how easy it is.

[8] The letter and response became a sensation after being posted on Upworthy and BuzzFeed and tweeted by George Takei.

[9] In 2009, Dickinson began asking her readers to wrap a book and put it on their children's beds on Christmas.

Dickinson asked readers of her column to give a book to a child on Christmas or whatever day they celebrated.