Advice columnist Amy Dickinson talks Katherine Hepburn, Tinder and how to handle the modern day heartbreak.

by Joanna Demkiewicz

Amy Dickinson of the syndicated advice column “Ask Amy” is not afraid of giving bad advice – literally. She told me, “Giving bad advice doesn’t even make the top ten of my fears,” when I asked about her biggest fears in life (they are the prospect of illness, disability, loss and death, by the way).

Dickinson took over the infamous “Ann Landers” advice column for the Chicago Tribune in 2003 after Esther “Eppie” Friedman died in 2002, and her column is now carried in more than 150 newspapers nationwide. She’s written on fashion choices for a “gender fluid” teen, what to do when you serially date losers, and how to politely opt out of crowdfunding a nephew because, hey, you just don’t want to. She gives advice fearlessly and doesn’t cushion any blows – perhaps because she doesn’t hold any illusions that she knows it all. She’s simply a professional listener, and a very good one at that.

Outside of her “Ask Amy” life, Dickinson is an NPR contributor and an original “Wait, Wait… Don’t Tell Me!” cast member. She published the acclaimed The Mighty Queens of Freeville: A Story of Surprising Second Chances in 2010 and is currently working on a sequel.

Here, she discusses how the advice column business has grown because of social media and why now is the time where conversations worth having – about campus rape, hookup culture and transforming gender roles in relationships – are finally the hot topics.

Joanna Demkiewicz: You’ve been an advice columnist for more than 10 years. From an observational standpoint, how has the public’s interpretation/opinion/idea of love changed (if at all) with the introduction of dating apps, new cultural discussions, etc.?

Amy Dickinson: Well, I don’t think Ann Landers – or I, 10 years ago – ever imagined a world with Tinder. In my time writing this column, I think I’ve seen the emergence of the hookup and witnessed the relationship challenges brought about by that kind of connecting – and now I feel we’re in this beautiful heightened awareness of the connection between friendship, sex, love and commitment. This has brought up myriad questions, which I can only try to tackle in my own way, using my own sense of ethics, combined by some viewings of (HBO’s) Girls, lots of reading, and experiences with five young adult daughters in various stages of relationship development. Conversations about campus rape, catcalling – these are good conversations for women to be engaged in. And reading about men, talking to men, and realizing that they, too, are at a cultural crossroads where roles and expectations are in flux. It is all good, and it seems to be moving and shifting quickly.

JD: More broadly – how has the advice column business changed in the 10 plus years you’ve been “Ask Amy”? Facebook was founded in 2004 and Twitter two years later. Are there simply more questions because readers have more ways to reach you? Also, are there more topics to be discussed?  

AD: There are more questions because there are more ways to reach me, and there are more questions because people have more ways to reach each other. If I had a nickel for every question about people connecting and having flings through Facebook… and people feeling dissed on Facebook, and kids being bullied on Snapchat, and people texting during dinner… social media has created wonderful connections, and whole new ways for people to drive each other crazy.

JD: In this Mashable article about you and other advice columnists, Emily Yoffe (“Dear Prudence” for Slate) juxtaposes being a journalist and being a therapist. What aspects of being an advice columnist are journalist-related and what aspects are therapist-oriented? What is the key difference between the two, and how are they related?

AD: I hesitate working from a construct that somebody else has introduced. I do a lot of research and reporting for my answers to questions and frequently quote experts or researchers on a particular topic. That’s the journalism part. In terms of “being a therapist,” I’m not a therapist. Not at all. But I am a great listener and I think people know that when they pose a question to me I will pay attention, take them seriously and be respectful in my answer. That’s also what a good therapist does (but I’m not one).

JD: What is the most frequently asked question readers send you? Why do you think this particular question/problem is so universal?

AD: Honestly, all of my questions are really about relationships – but mainly they are about boundaries. Can I tell someone something they don’t want to hear? How can I get someone to give me more/less space? How can I make love stay? How can I heal from grief? How can I face something impossible to face?

JD: What’s the one thing you wish everyone knew about the modern day heartbreak?

AD: I learned this the hard way, but modern day heartbreak is probably a lot like ancient heartbreak – mainly it fades in time. The heartbreak passes, like a storm of grief. And you can only glean what lessons there are in order to learn from it as you heal.

JD: What is the ugly side of working in the advice business? Be honest.

AD: I don’t enjoy people assuming that I am a know-it-all. Sometimes people make unkind assumptions that I am somehow not quite a “real” person, that I don’t have problems, that I must have the world completely wired. I feel this is dismissive and fairly hurtful.

JD: If you could receive life advice from anyone, dead or alive, who would it be and why?

AD: I think I’d turn to Abigail Adams, Katherine Hepburn and my mother – all wise, smart, practical, creative and flinty women. My mother, especially. I would give anything to be able to talk to her again. I was incredibly attached to her and I miss her every day (she died four years ago). She was wonderful.

JD: What’s on your bedstand right now? Who are some of your favorite writers?

AD: On top of the pile is Codependent No More: How to Stop Controlling Others and Start Caring For Yourself, by Melody Beattie, the classic self-help book describing the phenomenon of codependency. Just under that is Man’s Search for Meaning, Victor E. Frankl’s account of surviving the Holocaust. Currently, I am reading Neil Gaiman’s The Ocean at the End of the Lane: A Novel. My favorite writers are Mary Oliver, Billy Collins (I read a lot of poetry), Virginia Woolf, Michael Chabon, David McCollough and Nora Ephron.

JD: Describe your job in a tweet (140 characters or less).

AD: I help people untie knots, and also tie them. @AskingAmy (by the way)

Photo credit: Clara Gallagher

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Joanna Demkiewicz is The Riveter‘s co-founder and features editor. Find her on Twitter at @yanna_dem.