Amy Dickinson

A project of the Chicago Tribune, in conjunction with Agate Publishing, Ask Amy: Advice For Better Living (Midway, 2014), compiles several columns featured in the "Ask Amy" column by advice columnist Amy Dickinson. In the book, Dickinson, who also authored the recent memoir, The Mighty Queens of Freeville, provides insightful and intelligent guidance on a variety of themes, including family, dating, work, boundaries and life online. There are even questions and answers pertaining to LGBT issues within the book. Dickinson's embrace of the LGBT community, which differs greatly from her late-to-the-table predecessor, Ann Landers, recently made headlines when she set a parent straight, so to speak, regarding their homophobic treatment of a gay son. I spoke with Amy in January 2014 about the book and her column.

GS: (Gregg Shapiro) In addition to your "Ask Amy" column, many people also know you from your time on the public radio program "Wait, Wait Don't Tell Me". What do you enjoy most about doing that show?

AD: (Amy Dickinson) I have to say, especially given what I do for a living, to be able to go on stage and laugh and crack jokes and to be around these other people who are so funny and fun, it's a complete joy. I fell into that opportunity and it's made me really, really happy. You can tell. I've become known for, I guess, my giggle and my laugh, which I keep trying to suppress [laughs], but I can't seem to do it. Last week I was on. I was sitting next to Luke Burbank. His bluff was so funny that we had to stop tape while I had to collect myself. I was literally sitting up there and could not get it together. It's a complete joy. It's work too. I'm one of the few non-comedians on the show. I know a lot of comedians now and making comedy is hard work. Whenever I talked to Brian Babylon or Paula Poundstone, these are people who work so hard. I feel really fortunate because I can just sort of phone it in once a month and I don't have to go to Scranton, Pennsylvania and Mobile, Alabama.

GS: You don't have to work the comedy circuit.

AD: Oh, my God, they work so hard! I cannot get over it. But it's a total joy and a blast.

GS: Prior to becoming an advice columnist, were you someone people would come to for advice?

AD: No [laughs]. I would say no. I'm the youngest in a large family and I'm more likely to take advice and ask for advice than to offer it.

GS: Do you ever hear back from the people whose letters you use in your column?

AD: I do, but it's pretty rare. But it's very gratifying when it does happen. One I'm thinking of is the guy who wrote to me and he said, "What am I supposed to do? Everybody in my family tells me I have a drinking problem. But I don't have a drinking problem." I responded and said that "if everybody in your world tells you that you have a drinking problem, you do have a drinking problem. They are being pretty brave to disclose this to you and to try and talk to about it. You should respect that." Anyway, he wrote to me about a year later and he said that he was shocked when he saw my answer. It was like a slap in the face. He had gone into rehab and he was doing well. That was great [laughs]!

GS: You must feel like you've made a difference.

AD: Yes, I really do feel like that made the difference there.

GS: Do the questions come to you in the state we see them in the paper and in the book or is there some editing work done to them?

AD: Actually, there is very little editing. That is a choice I made when I first started writing the column because I really like the way people express their own problems. I think they are very revealing in the way they choose to write describe their own problem. I trim for length and I changed identifying details, such as if someone says a specific city, I will change that because I don't want for people to get burned by their own indiscretions. But otherwise, I do very little editing.

GS: Throughout the book you give succinct answers to the questions. Have you ever found it necessary to give a longer than usual response?

AD: Yes. I'm a little trapped in the format that I been provided with. I wish, and I thought about trying this, that once in a while I could just do one Q & A. My column is about 700 words and there are times that I wish I could just do one Q & A. As it is, my answers tend to be longer than in other advice columns in newspapers. One of the great things about online is that you don't have length constraints. [Laughs] I heard from a reader once years ago who said something like, "Your answers are so long. So many words. It just requires so much reading [laughs]." I'm like, "God forbid you should be reading all the words in the newspaper" [laughs].

GS: Earlier you mentioned removing identifying characteristics such as names of cities. Does geography play a role, as in is there one part of the country that reads and writes to you for advice more than others?

AD: Actually, I haven't noticed that. The column is very national. Now it's also in Canada. It is interesting in that a letter from San Francisco does tend to be different from a letter from Fort Worth, Texas. I really notice that. But otherwise, no, I don't hear from anyone part of the country more, I don't think. Most people don't say were there from.

GS: Does gender play a role or are questions received from both women and men equally?

AD: I would say it's two-thirds women writing. It's interesting, because you can control to a certain extent who writes into the column by the letters I carry. I love communicating with kids, so when I run a question in my column from a kid, other kids will write in. Very early on, I started deliberately running a lot of letters from men because I want men to write to me. I do feel I can made an impact in terms of opening up the column to men.

GS: That's great.

AD: In fact, Gregg, you know the letter (from the homophobic parent) that went viral? That parent who wrote in was a man. I'm 90% certain. A lot of people assume that that's a mother. I've communicated with the person a couple times, emailing back and forth before I ran the letter, and I'm pretty sure it was written by a dad, not a mom.

GS: I'm really glad you brought that letter up because you recently made quite a splash with your response to that homophobic parent regarding their gay son. Have any other letters gone viral to this extent?

AD: No! Oh my God, no! I have not changed my stand, so to speak, on LGBT issues in 10 years. 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. I'm really out there on social media and you can tell people who are cynically trying; it's pretty sad.

GS: It would be obvious when it's a plant as opposed to the real thing.

AD: Right. First of all, I'm actually sitting here with my laptop open looking at my mail. I need to clean up my email box but I have 31,442 emails in this email box. I don't need to look very far for people who have problems [laughs].

GS: In light of the recent letter regarding the gay son, would you mind saying something about your relationship with the gay community?

AD: I feel sometimes like it's hard for me to describe. First of all, I feel like the gay community is just looking for people to love, in a way. I feel that I have been embraced, honestly, for no particular reason, just because I'm a decent human being. I would say that this is the most significant cultural issue in my professional life. That over 10 years the LGBT community has just grown, blossomed, changed and come into its own. It's a really beautiful thing.