▸ Column · Modern Gotham — an underworld advice column read by the city's two feuding crime emperors

THE RIDDLER replies.

Replied to by The Riddler, with a rebuttal from The Penguin.

The letter

My split from Hadley went final fourteen months ago — nineteen years, gone with a judge's signature. My sister built me a profile on one of those matchmaking apps "as a joke," and I can't make myself delete it. The idea of sitting across a candlelit table from a stranger here in Gotham makes my stomach plummet like a dropped elevator. I've forgotten how to flirt, or whether anyone could still want me. Last week a gentle-sounding fellow named Osvaldo wrote "hi, how's your weekend?" — and I stared at it for three days, then shut the phone off and went to bed at eight. I keep saying I'm not ready. But I'm forty-six, not ninety, and some furious little part of me hates that fear gets to run the whole show. How does a person dive back in when even a friendly hello feels like the high board?

The Riddler replies

Aha! Listen to your own riddle: "How do I get back out there?" — flat, lazy, the question of someone hoping I'll hand over a stranger's phone number like a party favor. You don't want my answer. You'd never deserve it asking like that. So sharpen the thing.

Here's your real puzzle: you stared at "hi, how's your weekend?" for three days. Three days! Tell me — what did you mistake that hello for? A final exam. One right answer, graded by a judge, and you've already survived one of those, haven't you? Nineteen years, dissolved by a signature. You decoded the hardest cipher Gotham ever handed you and walked out the far side still breathing.

So riddle me this: when is a high dive not a high dive? When you stop pretending there's a wrong way to enter the water. A hello is not a test. It's a clue — proof someone, somewhere, is curious about the puzzle that is you.

You said fear runs the show. Good. Be furious. Fury is data; gut feeling is fog. The board you're terrified of is six inches off the ground. Look down. As I knew you would.

The Riddler

The Penguin weighs in

Waugh-waugh! Leave it to Nygma to answer a frightened soul with a crossword. "Look down," he coos — while you bleed sympathy all over a man who hasn't bought you so much as a drink.

My dear, you've buried the lede yourself: the fellow is named Osvaldo. A name of breeding, nearly my own — a gentleman, one prays, with assets. Stop confessing your terror to strangers; vulnerability is the umbrella you hand someone right before they leave you in the rain. Walk in owning something he wants — wit, mystery, a table he'd kill to sit at. And that sister, the one who made you a joke? Repay the jest, with interest. Waugh!

The Penguin

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