Congratulations on the movie and the new show! The first episode was so raw and poignant; it really caught me off guard, in a good way. What made you and Steve Almond decide to bring Dear Sugar back as a podcast?
"When I revealed my identity in 2012, I had every intention of continuing the column. But, it was also right before Wild [the book] came out, and I had no idea that it would become this big bestseller that demanded a lot of my attention. So, time passed, and I always felt like I hadn't quite finished Dear Sugar the way I wanted to.
Does it feel different to do the podcast without that veil of anonymity you had with the column?
"No, I never felt like I was writing through a veil of anonymity. I know that other people experienced it as such, but I was always very clear from the outset that I would put my name on those columns, someday. So, it never felt anonymous to me, if that makes sense.
I often write about personal issues on our site, and it’s a double-edged sword. It creates such intimacy with the reader when you expose your own deep, dark corners. But, there are ramifications in your personal life because there are other people in those deep, dark corners with you. How do you feel about that self-exposure in writing your memoir or doing the podcast?
"There's no question: That’s the hardest part of it. I mean, it really is. I care deeply about not hurting people and not invading their privacy. There are a couple horrible people in my life [laughs], and I have a right to speak my truth about what they did. In one case, I didn’t talk about it at all, and in the other I did it very carefully, because of the various consequences.
Right; you don't want to blow up somebody else's life because you're sharing their secrets.
"Well, unless if it affects your life. There's where it gets complicated. There are some things I wrote about my brother in Wild, where if you read carefully, you can surmise some of the struggles that he may have had, which impacted me as well. But, with each draft of my memoir, I took stuff out about him. Because, I didn’t have the right to tell the world his story.
Another great thing about Dear Sugar is that you honor that ambivalence and uncertainty. For example, in the first episode, you and Steve discussed the quandary of possibly having a third child in your respective families. You wound up in different situations there.
"Yeah! And, the thing is, we were both right. Steve and [his wife] Erin would be fine if they'd decided to have just two kids, and Brian [Cheryl’s husband] and I would be fine if we'd decided to have a third. Something different happened in each of our lives. So much of life is like that. Trust me: The year I was 40 and thinking, Do we want a third child? I spent days agonizing over that question. Now, I can have a total nonchalance about it. It would have been fine if we'd had a third child. I would just be slightly more grumpy right now than I am already [laughs]. I would also have this other person I love madly. You know what I mean?
"Oh yeah. Like, whenever I worry about my kids — wondering if they’re spoiled, if they’re brats, or why aren’t they listening to me. I think, Okay, are they probably going to be fine in 10 years? Yes. The answer is always yes.
That's a good reminder, because we make a million little decisions every day. Sometimes, it feels make-or-break, but when you step back and frame it in the long term, everything changes.
"Yes. Another great thing about the long view is that it allows you to figure out what your real feelings are. For instance, friendships. You know, when you're really annoyed or offended by a friend in the moment? Sometimes, I'll think, What if I got a phone call and found out that they died? What would I be feeling at their funeral? Usually, I realize that I would just be feeling how much I love that person, and how awesome that person is. It really helps you forgive the imperfections of life, when you take a longer view."
Sometimes, I'll find myself answering a reader email or giving a friend advice that I, myself, really need to take. Do you ever find yourself in that situation?
"Oh, all the time. These questions I get — they're the stuff of life, including my own life. For instance, all these questions about love and long-term relationships. So many people write to me and say they love their partner but they’re not in love anymore. They haven't had sex for ages. The romance has gone away. You hear this over and over. And, the problems are each different, but the baseline question is always the same: How do we keep romance and sex alive over many years in monogamy? That is a huge question. I want to answer it, not just for the listeners. I've been with my partner for 19 years; Steve has been with his for 15. We're there, too. How do we do this?
Well, it's helpful! The high horse is helpful when you have it available to climb up on.
"Right, and the only way that I got to the high horse is that I had been down in the mud, just like the letter-writer. In those cases, I was like, 'I'm going to give you a talking-to. Here's how you succeed. Not by sitting there, whining about what you think you deserve.’"
The New Yorker once wrote that many of the readers appear to be seeking your validation or attention, and maybe even your scolding, rather than advice, per se. Do you see a lot of that in the letters?
"Sometimes, yeah. People came to trust Sugar as someone who would be both loving and honest. Scolding might be too strong a word, but…no, you're right, I was scolding in those letters. But, it wasn't condemnation. It was affirmation. Sometimes, affirmation can be harsher than we think it is.
It’s true. Sometimes, self-help can foster a kind of narcissistic passivity.
"Yeah! So, I do think you should accept yourself. And, I do think that you should strive to be better. And, I include myself in that. You always need to be conscious of the ways in which you are in contradiction to the ethical or moral values that you espouse."
I think of the columns as something akin to a firm shoulder-shaking. Often, it's as if you're saying, ‘Come on, you know the way. Be honest.’
"Yup. So often in the questions, people basically tell me what they already know to be true. They're just afraid to know the truth. ‘I know I need to do this, but it's so hard.’ They need someone to say, 'Yep, it's hard. It's hard, but you've gotta do it, because it's harder not to.' You reach that point in your life where it's harder not to. Some people spend 50 years waiting to reach that point. Some people never do it. But, you always know.