Philly’s R. Eric Thomas is taking over the ‘Ask Amy’ advice column

Next month, after 21 years on the job, Amy Dickinson will end her tenure as the writer of the popular “Ask Amy” advice column. And a Philadelphian will be taking her place.

Dickinson announced her departure last week, saying R. Eric Thomas, a South Philly resident by way of Baltimore, would succeed her. Thomas will take over the column, which the Tribune Content Agency runs in 150 newspapers serving an estimated 22 million readers, on July 1, when it will become known as “Asking Eric.”

Thomas, 43, has a long history in Philadelphia, and is perhaps best known locally as a fixture in the performing arts scene. For the past decade, he has hosted the storytelling series The Moth — even after he left in 2017 for his native Baltimore, where he stayed for five years before returning to Philly. And he has penned a number of locally produced plays, including the 2016 Barrymore Award-winning Time Is on Our Side and An Army of Lovers, which debuted at Azuka Theatre this month.

Nationally, though, Thomas had made a name for himself with an often-viral column at Elle, a stint at Slate’s “Dear Prudence” advice column, and serving as a screenwriter on shows like FX’s Better Things and Apple TV+’s Dickinson. Thomas’ work also includes two memoirs — Congratulations, the Best is Over! and Here for It, or How to Save Your Soul in America — a 2020 biography of Rep. Maxine Waters, and a young adult novel, Kings of B’More.

Now, with Thomas poised to take over one of the most prominent advice columns going, we caught up with him to discuss what led him back to Philly, his take on advice columns, and the best — and worst — guidance he has ever received.

This interview has been edited for length and clarity.

We had purchased a house in Baltimore County during the pandemic, and it wasn’t an easy fit for me. There was a little too much suburban yard work and whatnot. I was not cut out for mulching.

But the main reason was that as the pandemic started to change, we really missed our community here in Philly. [My husband] David was approached about a job in Swarthmore at a church working with youth and families, which is something he had really wanted to do for a long time. So, it’s a perfect confluence of things, and by that time I was working full-time as a writer, so I could be anywhere.

It’s interesting. I do these interviews about my job, and I’m like, “Well, I just follow my husband wherever he goes.”

I had been wanting to get back into writing advice ever since I wrote “Dear Prudence” back in 2022. It was just a fantastic experience for me, and it felt like a nice continuation of the work I had been doing for Elle writing my column.

They reached out to me when they found out Amy Dickinson was going to be retiring. They asked me to audition with a couple sample columns, and I didn’t really know what it was for for a long time.

When they told me, “Oh, ‘Ask Amy’ is ending and we’re looking for something to succeed it and reach similar audience,” I was like, “Oh, this is very big.”

Yeah. There have been different things in my career where I have been pleasantly surprised by the reach.

The books had a big reach, but that’s got a longer tail. My columns for Elle would go viral, but that’s a thing that kind of exists on the internet alone. This, because it’s in the newspaper, and there are hundreds of newspapers, it almost feels like it is stepping into a whole different world.

Advice isn’t a prescription. It isn’t going to the doctor. So, I’m not walking around with a pair of reading glasses and a prescription pad telling people what to do.

I am somebody who spent years going to therapy telling my therapist, “I want you to tell me exactly what I need to do.” Every therapist I ever had told me, “Well, I’m not going to do that.”

I’m like, “Well, OK, my insurance company, you will be hearing from them about this.”

But some people want you to tell them exactly what to do, as if it is fixing a carburetor. And life is just not that simple. Sometimes, it’s like, “You should stop seeing this person,” or whatever. But the thing about life is that there are no right answers.

And that’s kind of frustrating from the human perspective, because you’re like, “No, but what’s the choice that’s going to get me out of this jam?” There is none — this isn’t The Price is Right or Let’s Make A Deal.

You’re going to pick a door, you’re going to walk through that door, and you’re going to look around and figure out how to live with that choice.

Here’s the thing: I feel impostor syndrome all the time about everything. I feel impostor syndrome about things I have done and gotten awards for.

I think the impostor syndrome is helpful in this context because it reminds me to approach people’s questions with humility. Even if someone was like, “I need advice about how to get a nationally syndicated column,” I would be like, “I am not an expert on that.”

I think there’s no such thing as being an impostor, as long as you are being authentic. I’m trying to show up and be fully present and give people feedback.

I’m so curious about people. And the flip side of that is that I am deeply nosy. That’s where everything comes from. And I’m very interested in story.

I also am glad that I have written two memoirs now, and I will probably write another book of essays at some point. I wrote two books about making a massive number of mistakes over many decades, making the wrong choices, being the bad guy accidentally, and figuring it out. All that to say, what I am trying to become expert at is being a person who doesn’t always know what to do. And that is who writing into the column.

If I can get inside that feeling, I can figure out how to help other people get out of that space.

The best advice I ever received is also sort of the worst advice. I was going through this awful period in my early 30s, and things had started to turn around. I said, “I’m just always waiting for the other shoe to drop.”

[A friend] said to me, “There is no other shoe.” I found that to be revelatory — so it was good advice, because I was free. But then I thought, “Yes there is. How do you know? The world is full of shoes.”

He gave me advice that was true for him, but not true for me. It helped me to see the world in a different way — but I do think there is another shoe. Life is a DSW, and that’s OK. There’s plenty of shoes, and what I needed to do was figure out how to operate inside of a shoe warehouse.