Dear Auntie Screwtape

As a child, I read Ann Landers and Dear Abby with bafflement and excitement at the world of adult problems, which seemed to involve a lot of brothers-in-law and nude photographs. Gradually, I came to love advice columns as an artistic form. There’s a regularity to them that I find really comforting: someone writes in with a ridiculous tangle of a personal problem, and the columnist responds by methodically steering them back toward the world of sense. Some are pardon’d, others punishéd.

I’ve often thought that I’d like to write one myself. I know that Daniel Ortberg once wrote about how baffling Dear Prudence columns are, and now he is Dear Prudence, so it seems plausible to me that I could manifest my own by focusing my intentions. The trick to a successful advice column, if you can call something so fundamental a trick, seems to be finding a niche to be an expert in. Captain Awkward has claimed healthy boundaries and any situation in which an introvert is trying to get out of a social setting; Ask a Manager has the norms of the business world pretty well sewn up. So I have been trying to think of situations I am uniquely qualified to address, should anyone decide to ask me about them:

You’ve recently started taking salsa lessons at a nightclub where the doorman is a former student; how much hip movement is permissible?

Your ex-lover and their new lover are coming to town, and they want to take you to dinner. Is this, you know, a Thing?

After nine years, your mother still hasn’t called you by your chosen name. How many days per year, on average, are you obligated to spend working in her coffee shop?

You’re having a party and you’re trying to impress someone, but like not impress that person too much, like, you’re really content and you don’t have a lot of room in your life but that PERSON is coming over and so what shirt do you wear? Like a t-shirt but maybe a cropped one? Or like something with some birds on it I don’t know maybe just that black shirt but that’s kind of work-y

You had to kick someone out of your Dungeons and Dragons group after a long period of growing resentment. How long should you keep the decaying receipt for the last time they tricked you into buying them chicken nuggets tucked into your wallet?

While doing a Marie Kondo, you find an ugly thing given to you by someone you love more than words can say, and you hold it to your chest and sniff it and it still kind of smells like them, and you think about when they gave it to you and how you said you loved it, and you meant it then because you loved that it was a gift from them. Does that count as sparking joy?

One of your students won’t stop asking you questions and then interrupting you to tell you what he thinks you’re going to say next, while you just stand there in silence staring at him, waiting for him to realize what he’s doing, and he doesn’t? There’s no question here, just…I mean, argh, right?

If you are reading this and thinking “I bet Rose could address my concern”, drop me a line and I’ll respond to it in an upcoming newsletter. If you’re reading this and thinking “wait, am I referenced in this article?” the answer is: Darling, I’m sorry, I’m never wearing that sweatshirt again but I’m keeping it for the rest of my life. Forgive me.