Amy Dickinson knows the struggles of a middle-aged woman as well as anyone, and she’s not afraid to talk about it. There was the time the nationally syndicated advice columnist, then in her 40s, stepped into a drugstore in her hometown of Freeville, N.Y., and asked the pharmacist for both birth control and menopause remedies.
“Such are the joys of being a pre-menopausal woman, terrified also of pregnancy,” she relayed to a Rockville audience on March 14. “The person waiting on me was, of course, someone I know. And she was like, ‘Oh my God, you went to school with my mom.’ And then she’s like, doing the whole thing that you dread into the microphone. Like, ‘do you have any sponges in the back?’ It was a nightmare.”
There is a method to Dickinson’s outspokenness. She helps readers of her column, which appears in The Washington Post, find answers to life’s most nagging questions, and does so by examining her own life’s ups and downs.
“I’m often asked how I know what I know,” she said. “I’m not a psychologist or a member of the clergy. I don’t have an advanced degree. The fact is, I got here the hard way.”
Dickinson was speaking to a mostly female audience of about 60 people, hosted by Charles E. Smith Life Communities. The columnist touched on the more serious moments during her 30s, 40s and 50s such as moving from city to city, divorce, single motherhood, remarriage and taking care of her ailing mother — all subjects in her 2017 memoir, “Strangers Tend to Tell Me Things.”
Dickinson, 58, sprinkled just enough humor at the end of each sentence to elicit a few laughs, despite the heavy subject matter. Her first marriage, to CBS news correspondent Anthony Mason, had “the shelf life of a wheel of Brie.”
Starting over, Dickinson said, has been a theme that has run through her life. Her mother raised her and her three siblings as a single parent after her father abandoned the family. Jane Dickinson later earned a master of fine arts degree and taught for 15 years at Ithaca College.
Amy Dickinson moved from New York City to London to Washington and then, eventually, back to Freeville, all while raising her daughter, Emily, as a single mother. She freelanced for several newspapers, gave commentary for National Public Radio and for two years was a columnist for Time before becoming the Chicago Tribune’s syndicated advice columnist in 2003, following the death of Esther Lederer, better known as Ann Landers.
Dickinson continued to have ups and downs, from the joy of marrying her second husband, Bruno Schickel, in 2008 to the difficulties of taking care of her ailing mother around the same time.
How then, with all of that activity, does she find a way to crank out seven columns a week helping others solve their problems?
“I put my own problems very much on the back burner,” she said. “The reason is simple: It’s so much easier to focus on other people than to heal what ails you.”
Asked how she chooses which of the 200 to 300 emails she receives every day to respond to in her column, she said her choice often comes from personal experience.
“Sometimes I’ll choose the letter because it’s something I’m struggling with, and sometimes I’ll choose a letter because it’s something I feel I really own,” she said.
Does Dickinson edit the letters she runs? Only for grammar, she said.
Dickinson also said she responds to letter-writers who are in distress, but instead of publishing the letter she will contact the appropriate health professionals or people in the community that can help, such as a guidance counselor for a teenager who is struggling with depression.
“I will get right back to them and say, ‘I see you. I hear you. I’d like to try to help,’” she said. “And I will engage in a dialogue with them that lasts a couple of days.”
Diane Stern, the administrator at the Hebrew Home of Greater Washington, said she liked Dickinson’s down-to-earth delivery.
“A lot of her life experiences are something each of us could relate to,” Stern said. “A lot of it was very sad, but she had a positive attitude, which we all need to do.”
Jacqueline Rams, the vice chair for development at Charles E. Smith Life Communities, said she enjoyed Dickinson’s mix of serious and lighthearted vignettes.
“She was terrific,” Rams said. “Funny. Joyous. Sad. But it always came back to being funny.”
And at the end of the day, Dickinson’s dream might be the same as everyone else’s.
“If I could live my best life, I would live on my couch watching Judge Judy and eating Cinnabon,” she said. “But it seems that others most often make the choices for us, by loving us or leaving us.”