Dear Prudence: The Column: The Book Is Out April 4th

“I want to be right all of the time; in my natural condition and given the option, I would choose the warm satisfaction of self-righteousness over happiness ninety-nine times out of a hundred. I recognize this impulse is at best maladaptive and have the necessary system of pulleys and emotional riggings in place to counter it, but I feel a keen sense of loss whenever I come across a letter where someone has blundered their way from being entirely, unequivocally right to merely half right or, worse, in a position where they have to apologize to someone they dislike.”

Interested parties should note that in a little over a month from now, April 4th, will see the publication of Dear Prudence, an anthology-slash-retrospective of my tenure as Slate’s advice columnist from 2016-2021.¹

You can pre-order a copy at Books-a-Million, Bookshop, or Amazon. The audiobook, read by self, is also available for pre-order, if you’d rather hear that.

“The inside of our own problems can feel like such a vast and complicated place that it’s tempting to assume nobody else experiences such a dizzying array of weights and counterweights, regrets and bitter-shot pleasure, abeyances and complications; that everyone else gets what they want in a straightforward, immediate way as soon as they realize they want it; that we alone are conducting a tortured symphony of sentiment with a thousand different musicians while everyone else is playing “If You’re Happy and You Know It” on a child’s xylophone. I do it all the time. I’m never right, but I still do it all the time.”

More details to come as April approaches, but I’ll be doing at least one event in-person in New York City, a virtual event in Atlanta, and a library event in Connecticut that week. Later in May I’ll be at the Sydney Writers’ Festival in Australia and the Auckland Writers’ Festival in New Zealand, so please come by a panel or two if you happen to be in the neighborhood.

Chapters include:

• What Time’s the Next Swan?

• Can I Break Up With Him Without Hurting His Feelings?

• Just One More Thing

• The Care and Maintenance of Your Estrangement

• It’s Fine If You Want To Transition, It’s Just That —

• The Other Shoe Just Dropped

You get the idea. A bit pithy, and with a nice little Walter Slezak reference. (I had to look up how to pronounce Slezak while I was recording the audiobook, since I’d only ever seen his name written in the credits at the beginning of his movies, and can’t promise you I got it right. There are two or three French phrases in the book, too, that I now bitterly regret ever having included, because try as I might I just can’t say cycliste properly, but there you are.)

There’s a bit of meta-analysis as well, as I revisit some of the advice I might wish to modify in retrospect and the experience of transitioning, then becoming quite publicly estranged from my own family, while on the job.²³

“My own estrangement was not an act of personal punishment…I would not, could not, simply take my brother and the rest of our family at their word that their secret strategy was safe or sane and that only people with the last name of Ortberg were entitled to know about it…I heard from many letter writers over the years in ghastly, similar situations, many of them much worse than my own. ‘Keep the secret and we will love you,’ the promise goes, ‘but step outside the family circle and there’s no telling what might happen to you.’ For my part, in my own limited and imperfect capacity as an advice giver, I cannot promise much — I can promise that estrangement is possible, that it is survivable, and that other forms of relation and kinship and reciprocity exist on the other side. Beyond that, I cannot say for certain; I cannot guess what gains might come to balance the losses for any given person, if leaving will come to feel like a relief or a suppurating wound or something else entirely…but it can be done, and it can even be good. Not always good, nor thoroughly good, but one can find real and surprising sources of goodness in it.”

If you don’t wish to purchase the book, allow me to recommend Jenée Desmond-Harris, Slate’s current Dear Prudence, or a secondhand copy of Ann Landers’ Since You Ask Me, a very charming advice anthology from 1961. But if neither of those appeal to you either, you’re on your own; I can’t spend all day guessing things you might like.

1. I didn’t choose the subtitle, it’s a perfectly fine subtitle I’m sure but I don’t know whether any of my advice was especially “liberating,” and of course one can’t refer to oneself as a beloved anything.

2. I certainly wouldn’t recommend it, but it all seemed to work out reasonably well in the end.

3. To be clear, I really do mean a bit only, so don’t get too excited for gory details.