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Amy Dickinson looks back on 21 years writing her advice column 'Ask Amy'

SCOTT SIMON, HOST:

I've got a question to ask now - dear Amy, why are you leaving "Ask Amy"? Amy Dickinson is leaving her widely syndicated "Ask Amy" advice column for the Chicago Tribune at the end of this month. For 21 years, she's offered advice about love, marriage, transitions, friendship, relatives, and relationships, broken hearts, bruised feelings, work-life balance, coming out and stepping up for people. Amy Dickinson joins us from New York. Thanks so much for being with us.

AMY DICKINSON: Hi, Scott.

SIMON: Why are you leaving?

DICKINSON: You know, it's so funny - at my age, people keep congratulating me on my retirement. And my answer is, no, dude, I'm quitting. I quit. I mean, I wanted to be maybe the first advice columnist ever not to die at her desk.

SIMON: (Laughter).

DICKINSON: And honestly, I think I took really to heart - I have taken to heart the lessons I've learned from giving advice. And here's what I know. I get one life, and I have plans. So I'm leaving.

SIMON: Can we ask what the plans are?

DICKINSON: Yeah. I am opening a little lending library in my hometown. And I'm really committing to, you know, trying to get kids in after school. I want to sell candy. But also, I plan to write books and really just take a lot of what I've learned over the last 21 years and apply these things to my own life.

SIMON: What kind of responsibility is it to offer advice to people - no, not about cooking or clothes or even politics - but the most intimate and compelling questions of their lives?

DICKINSON: It's huge. It feels huge. But, you know, and in this regard, I go back to something Ann Landers said to her longtime editor, Rick Kogan, in Chicago. And Rick passed this along to me when I first started writing this column. And he said, Ann Landers said to me, these problems aren't my problems. I have my own problems.

SIMON: (Laughter).

DICKINSON: So often I have gone back to that because I think it really is necessary to learn how to detach, how to be helpful as much as you can, but life goes on.

SIMON: Let me ask you about one of your most quoted and noted replies. November 2013, a parent who signed Feeling Betrayed said he wanted his son to, quote, '"stop being gay." Do you remember what you told him?

DICKINSON: I actually emailed back and forth with that man a few times because I really wanted clarity. Like, I sort of couldn't believe it. And I said something to the effect of, I have an idea, why don't you stop being straight, and then you can show him how easy it is. So, yeah. That was a good one.

SIMON: Just between you and me, as they say, (laughter) did you ever get sick and tired of being asked for advice?

DICKINSON: Yeah. Yes, honestly. And, yeah, it is sort of exhausting. And, Scott, I mean, come on, some of these trends - like gender reveals - I cannot believe that I have had to take questions from people about challenges related to their gender reveal parties. It's so stupid. I'm like, here's my advice to you, never do that.

(LAUGHTER)

SIMON: This is a tough one. Have you ever regretted any advice you've given someone?

DICKINSON: I have. I absolutely have. I can honestly, though, only think of one time when I have regretted something I had published. But I will say, in that case, I was very much in touch with the person who wrote to me. And that person did not feel that I made a mistake. But the rest of the world did.

Oh, wait, OK, I have a couple of - I've been pranked. So...

SIMON: Really?

DICKINSON: ...A classic way to prank an advice columnist is to base your question on the plot of a television show or a movie.

SIMON: (Laughter).

DICKINSON: So I caught one that I know "Dear Abby" did answer. I caught one that was obviously based on an episode of "The Simpsons." But I missed one that was based on a famous episode of "Seinfeld." And I ran the question as if it was legit, because I thought it was. I answered it. And oh, my, the reaction was - when this was published, was instantaneous. You know, Amy got pranked. It was so hilarious. Yeah, that was no fun.

SIMON: I don't know a better way to put this. How can people be happy?

DICKINSON: Yeah. It's such a great question. I will tell you how I've done it, and I have done it. And my mother did it, and I watched her do it. You become a miniaturist. You look for the small things to value. You look for the tiny episodes of beauty. You find something or someone to take care of. And you sink back and accept your humanity, your flaws. And you, you know, be gentle to yourself and to others. That's how to do it.

SIMON: Well, thank you.

DICKINSON: Thank you, Scott.

SIMON: Amy Dickinson, "Ask Amy, " leaving her column at the end of this month to run a library, write books. Hope we talk to you again. Thanks so much.

DICKINSON: Oh, my God. Now I'm crying. OK. Thank you, Scott.

SIMON: Me too. Me too.

DICKINSON: Oh.

SIMON: (Laughter) But you know, it's not hard to make me cry.

DICKINSON: I know. We're both such blubber babies. Oh, my God. All right. Well, thank you so much.

(SOUNDBITE OF MUSIC) Transcript provided by NPR, Copyright NPR.

NPR transcripts are created on a rush deadline by an NPR contractor. This text may not be in its final form and may be updated or revised in the future. Accuracy and availability may vary. The authoritative record of NPR’s programming is the audio record.

Scott Simon is one of America's most admired writers and broadcasters. He is the host of Weekend Edition Saturday and is one of the hosts of NPR's morning news podcast Up First. He has reported from all fifty states, five continents, and ten wars, from El Salvador to Sarajevo to Afghanistan and Iraq. His books have chronicled character and characters, in war and peace, sports and art, tragedy and comedy.