When Anna arrived at the castle, the air was ripe with thunder. It wasn’t supposed to rain — there’d been no thunderstorm in the original novel. Even the threat of rain could prevent the moonlit walk that Miss Pennyworth was supposed to take with the Duke.

Lightning arced through the sky as she exited the carriage. Anna checked that her ballgown was straight before she followed Miss Pennyworth’s aunt into the castle.

“Lady Ashby and her niece, Miss Pennyworth,” the majordomo crowed, and Anna curtsied to the Duke. He had golden hair, green eyes, and a dashing eyebrow scar from a duel gone wrong.

“Stop gaping like a fishwife,” Lady Ashby said.

Anna looked at him as Lady Ashby pushed her forwards. By the waltz on page 254, their eyes would lock. Her anxiety kicked in, and she forced herself to breathe slowly. Her insides felt like they were filled with jumping spiders.

The ballroom was packed with silk and jewels and a thousand candles that reflected in the raindrop-strewn windows. It stank of humanity, of perfume and sweat, and words shouted over lemonade glasses. The orchestra began to play. Lady Ashby consulted Anna’s dance card, and practically shoved her into the arms of her first partner.

She danced. She flirted. She played the part of Miss Pennyworth to perfection.

Anna downed a glass of ratafia to settle her nerves.

“Courage, child,” Lady Ashby said, taking the glass. “The Duke desires to dance.”

Anna followed her gaze as he approached them in all his golden glory.

“Miss Pennyworth, I believe this dance is mine.”


They waltzed.

It was enchanting: the soaring music, his hand at Anna’s waist, the feel of him pressed against her. Her heart hammered in her chest, and the spiders started doing tarantellas.

“I need some air,” she said.

“Come to the garden. The rain will stop.”

Anna allowed him to ferry her outside. There were puddles everywhere, but the sky was suddenly dry.

“That’s not how the book goes.”

“Don’t be so literal,” the Duke said, steering her towards the night-scented tobacco.

He would kiss her there. His lips would press into hers, she would hear the swirl of violin music, and she would know that he was her destiny. The book-travel experience would be everything that her parents had paid for.

“How did you do that?”

“Magic,” he said, shrugging.

But life wasn’t magic. Life was anxiety and panic and dreams long delayed. She stopped walking.

“Miss Pennyworth?”

“My name is Anna.” She stuck out her hand for him to shake. He held onto it instead.

“Your Christian name is Elizabeth.”


“Miss Pennyworth, are you deliberately breaking character?”

Of course, she was. This was all wrong. Book travel was a fairy tale; a precisely calculated experience of computers and neurological sensations. It was a mistake to think that she could enjoy it. But still.

“Will you show me how you made the rain stop?” she asked, letting curiosity win.

The Duke grinned and snapped the fingers of his free hand; a light drizzle began.

“I’m very tired of romancing ingénues.”

“But that’s the plot.”

“Who said I had to follow the plot?”

“Make it rain harder.”

Another snap, another grin, and the Duke took a step closer. The spiders started to settle down.

“Are we going to stand here all night?” he said.

“Is this part of your programming?”

It had to be a clever algorithm crafted to react to a book traveller gone rogue.

“I’m a man with feelings.”

“Virtual feelings,” Anna said, blinking rain out of her eyes. It felt more real than anything else that had happened tonight.

“In this world — in this book — I exist, Miss Pennyworth. You’re the lonely intruder here.”

The AI was really very good. Perhaps too good.

The Duke tightened his grip on her hand; the rain had darkened his hair and streams of water were running down his neck. It only made him more appealing.

Anna turned her face up into the rain. She let it wash over her, let it consume her until the spiders disappeared. It was nothing like the novel, but that was what made it exactly right.

“Run with me,” she said.

Past the statuary, past the night-scented tobacco, past the entire formal gardens they ran. Anna’s dress was soaked and her feet slipped on the wet grass. It was exhilarating.

“This is better than the book,” she said.

“I never liked Miss Pennyworth.”

“You marry her. You carpet the church with roses on your wedding day.”

“But that’s not my story. I detest the ingénues, the endless balls, all of it. It numbs my mind, dulls my senses, makes me feel like nothing more than a construct of a man.”

Anna refrained from saying that this was true.

“Why don’t we get to choose how we write our own stories?” he continued.

He wasn’t real; he couldn’t be real. No AI was this emotionally complex. Anna held onto his hand anyway.

“Because sometimes, life doesn’t let us do that,” she said softly. “Sometimes, we need to follow the script. Sometimes, we don’t get a choice.” The spiders tried to come back and she pushed them down. Not now.

“I’m more than just words on a page.”

“But sometimes, we get to throw the script away.”

“Help me. Dance with me again, Anna.”

“I won’t be Miss Pennyworth when I leave.”

“You’re a million times better.”

“None of this will be real.”

“It’s real to me.”

“Do your magic again. Make it pour.”

As the storm raged, they danced. It was both real and not-real, and for one moment, she believed in every bit of magic.

Anna rose on her tiptoes to kiss him, to brand him, to claim him as her own. To make him remember her somehow. To give him this, even if she couldn’t do anything else.

She felt him smile as the rain poured down.

The story behind the story

Jenny Rae Rappaport reveals the inspiration behind Becoming Miss Pennyworth.

I wrote the first draft of Becoming Miss Pennyworth in January 2017, a month before I gave birth to my third child. I was very pregnant and dealing with complications from that, so the idea of escaping into a book was extremely appealing to me. At the same time, my online writing group was running a flash-fiction contest. Two of the story prompts for that contest were ‘Give us a hero’ and ‘Why do people like kissing?’, which instantly made me think of Regency romances.

A good book has characters that we fall in love with as readers — we root for them, we want to know them better, and we mourn when something terrible happens to them in the course of their story. It was simple extrapolation to imagine a technology that made it possible for readers to join those characters in their own worlds, even if only through a neurological simulation. And even more extrapolation to imagine that some of those simulated characters might yearn for sentience of their own — and perhaps, one day, achieve it.