Readers of New York magazine have been heeding the wisdom of Heather Havrilesky for years. A veteran journalist, Havrilesky is the voice behind the magazine's popular advice column, "Ask Polly." With her second book, How to Be a Person in the World: Ask Polly's Guide Through the Paradoxes of Modern Life (Doubleday) out today, we spoke to Havrilesky about what it's like to counsel the distressed and forlorn.

How did the book come about?

I knew I wanted to try to write some sort of “Ask Polly” book and I thought about trying to write a mix of essays and self-help, but I didn’t want it to be too much of a departure from the good things that were already happening at the column itself for New York. So I talked to a lot of different editors at a lot of different places, and my editor at Doubleday, Yaniv Soha, was very intent on keeping the exact format that was already working so well, and so I was like, ‘Well, I love writing the columns.’ So that’s what we did—I just wrote a whole bunch of new columns. I discovered that it was much better to simply answer too many columns, then go back and pick which one we liked the best.

What did you enjoy most about writing the column?

I like all of it. The days that I get to write the column are my favorite days. For some reason, the writing flows more than it does in anything else I do. There are just a million different things that can be brought into any letter and, if anything, I struggle to cut myself off at the pass when I’m going in too many different directions. That’s more of the struggle: too much information.

You also write a bestseller column for Bookforum. From doing this, have you picked up any insight into what makes a book a bestseller?

Very simple, flashy, groundbreaking-sounding one-subject books seem to sell, but then nine times out of 10 the books themselves are truly terrible—badly written, and flabby, and pointless. It would be nice if people were forced to read a chapter of any given book before they bought it. So many great books are neglected and so many terrible books sell like crazy, simply because the concept sounds sexy, or there's a celebrity author’s name on the cover.

As Polly, what's been the best question you've received?

I tend to love whatever questions I get each week, but there was one about, ‘I’m kind of a badass and I finally met a man who’s good enough for me, and then he dumped me. I don’t get it. Did he dump me for the zits on my jawline? What went wrong?’ I love letters like this, where there’s just a lot of tricking yourself and self-hatred evident. I’m attracted to letters where there’s a lot of inner conflict and noise going on.

This interview has been edited and condensed.