Jack had only been running Don Juan 2.0 for a week, and he was already getting hella action. The AI, which projected in his upper left field of vision as a tall, dark, handsome man in miniature, had successfully navigated him through three phone numbers, two half-drunk hook-ups, and one conversation in passable French with an aspiring model.

That was the only reason Jack thought he had even a chance with the woman on the café patio. She was beautiful in the way that launched ships, with an angel’s smile and bone structure won by genetic lotto or twelve rounds with Florida’s best cosmosurgeons. Jack felt dizzied by the long legs slicing out from her skirt, by the graceful hand managing her cascade of dark hair. Fortunately, Don was there to do the talking.

“I’ve seen better,” Jack’s mouth said, as he slid into the spindly chair across from her.

She gave a languid blink, dipping soot-coloured curtains over electric blue eyes. “Pardon?”

Jack was already extracting all kinds of disasters from the woman’s bored monotone, but in the rafters of his left eye-socket Don gave him a wink he’d learned to trust and laid out inflection for the next line. “The croissants,” Jack’s mouth explained. “They’re average at best.”

She glanced down at the pastry cooling beside her latte. Her beestung lips pursed. “You’re the second person to come up to me this morning like this.”

“To criticize the croissants?” Jack’s mouth asked. Don sent him on a biofeedback loop that tamped his nerves down. He let his hand splay flat and honest across the tabletop.

“To say something clever.” The woman smiled in a way that ached. “You wouldn’t be running a deejay, too, would you?”

Jack’s heart stuttered. He knew, vaguely, that Don Juan 2.0’s predecessor had been full of bugs, one of which included the inability to process self-referential information. That deficiency had been ironed out. Supposedly. Don couldn’t sponge the sweat from under his armpits, but he did move Jack’s jaws into a smile, sparkling and quizzical, and then …

“You’ll have to forgive me, I’m a bit of a Luddite. Is that one of those programs that shows you where the clitoris is?”

The woman’s wide blue eyes went wider and Jack wanted to vomit apologies, but Don shook his head, patted the air to say wait, just wait. The woman hesitated, then laughed, a trembling bubbling sound as if she was doing it for the first time.

Don knew. Don always knew. Jack finally breathed as his internal organs settled themselves.

“I’m Jack,” his mouth said while the iron was hot. His hand flipped over on the table, palm-up to be clasped.

“Alice,” the woman said, and dipped her immaculate hand into his.

On his way back to work, Jack’s feet felt like helium. The contact information of Alice Fenderi — quite possibly an heiress of the Fenderi Robotics Company, though Don had advised him not to ask — was burning a metaphorical hole in his cranial implant.

Upon entering the office he found his desk had moved itself again, as the modular units were wont to do following the new stress-reduction SynergySeeker algorithm, but he moved past its inviting rumble to the treadmill where Petr was crunching code.

Petr was the brains behind the Don Juan dating assistant and its as-of-yet unreleased iteration 2.0, and of course he was the type who’d probably never had a problem getting girls in his life: tall, Scandinavian, jaw like hewn rock and sea-green eyes that hell, even Jack caught himself getting lost in from time to time. But Petr was also the type who always thought there was room for improvement.

So, along with a half-dozen other AI programmers around the globe, he’d compiled hundreds of thousands of hours of film stars and field footage and broken it all down into response loops, body language and timing, dissecting the core anatomy of seduction. And then he’d built it back up in the form of a semi-sentient AI who could give Casanova, Don Draper, and Nicky Bricks a run for their money.

“Yo, Jack,” Petr huffed, knocking the treadmill back to a slow jog. “How’s my favorite beta tester today?”

“Petr.” Jack’s mouth was smiling without him or Don calling the shots. “Petr, you would not believe the woman I just met.”

And because he couldn’t wait, he sent an image of Alice leaning slightly forward, chin tilted just so, those eyes so sparkling coy and innocent at the same time, displaying the sculpture of her bared collarbone and just a hint of cleavage.

Petr blinked the image onto his retina, then his eyes widened. “Holy shit, Jack.” He shook his head disbelievingly; Jack sidestepped the sweat spray. “She’s perfect, man.”

“Well, Don did the talking, not me,” Jack said. “So … thanks. I’m really glad you got me to run beta on this.”

“Can’t think of a single person who deserves it more,” Petr said, cranking up the speed again. “Just have to get back into that dating pool, man. Enjoy the rebound. Go big. Give it another week and you won’t even remember your ex’s name.”

Violet. Petr was already pumping his arms and mouthing numbers again as Jack’s smiled faded. The notification he’d set up informed him, with a small burst of digital fireworks, that he’d gone an hour and thirty-three minutes without thinking about her. It was a new record, but it didn’t make him feel much better.

The glumness compounded when Jack got home and tripped over the plastic tub he’d set inside the doorway. Violet had moved out, supposedly, but three years together had resulted in the accretion of far more miscellanea than could be found in an afternoon. Now Jack picked the spilled mementos up from the carpet: a chipped blue mug, thermal socks, a print they’d bought from some street artist on holidays in Prague. It would take months to find everything, and Jack now realized the apartment had become a sort of emotional minefield.

He slumped down onto the couch Violet had opted to leave, closing his eyes and flicking through work messages. He couldn’t help but notice that their calendars were still linked — he could see her film club meeting on Thursday and the lime green bar that indicated she was currently swimming at the U. Maybe she’d forgotten to unlink them. Or maybe she’d left it on purpose, so he’d be able to see that, unlike some people, she hadn’t missed work for a week-long booze-fueled hibernation following the break-up.

Jack also couldn’t help but notice Alice Fenderi’s information sitting in its docket.

On cue, Don popped up in his peripheral vision. Time to make the call, Jack.

“Same day? Aren’t you always telling me to wait?”

Not for this one. Trust me.

Jack did. He closed the calendar, feeling only a slight twinge of regret when Violet’s name disappeared, took a deep bracing breath, and called.

Alice Fenderi was galaxies away from any woman Jack had ever been with. When she walked into the bakery where they were meeting for breakfast, the recording lights of about half the customers began to blink red, just in case she was a celebrity. Jack felt more than a little uncomfortable when heads started slyly turning towards him, too, but Don didn’t let him show it.

And she wasn’t just beautiful, either — the conversation was scintillating. Alice was keen, curious, and had a mischievous streak. She listened intently and questioned intelligently as Jack dipped into the more interesting aspects of his work in AI development, a zest explained shortly thereafter when she admitted to being a Fenderi of the Fenderi Robotics dynasty.

To his credit, Don stuck to a hands-off approach for the first twenty minutes, only feeding Jack a line when Alice’s crossed and uncrossed legs short-circuited him, and another to navigate a frosting-on-the-chin situation. Before long, however, Jack found himself the observer in a rapid-fire exchange on the philosophy of sapience.

Alice was terrifically out of his league in every conceivable way, but Don was there to keep him afloat, and breakfast ended with a spine-tingling kiss that went straight to his trousers.

“She already likes me,” Jack said, once she’d departed. “Or us. Or whatever. You could’ve let me get a word in.” He’d retreated to the bathroom to give his erection time to calm down, washing his hands for a good five minutes.

Jack, you just kissed the most beautiful woman you’ve ever laid eyes on in your entire life. Maybe a thank-you?

Jack gave his reflection a wry grin. “Yeah, yeah. Thanks.”

Had to seal the deal, that’s all. Now you’re set.

Jack flicked through his calendar to the drinks date he’d scheduled for next Thursday evening, just to see it again. It had taken some skillful manoeuvring around Alice’s work schedule: She spent a surprising amount of time at the labs, despite doing only “small calibrations, nothing too complex” — modesty again, Jack was sure.

He did a double-take. There, blocked in under film club, Violet had added an event: dinner with Landry. The past week of AI-assisted rebounding hissed away in a boiling wave of indignation that Jack knew, dimly, was hypocritical. It felt like he was back on the wordless drive to her sister’s place with his heart splintering into a thousand pieces, knowing in a deep and sickening way that things were really truly through.

So he barely even thought before he snapped off a message to Alice, changing the location of their next rendezvous.

Don raised an eyebrow, swished his virtual glass of scotch so the virtual ice cubes clinked. Bit petty, don’t you think?

“Okay, Jiminy Cricket,” Jack mumbled, drawing a glance from the man beside him at the hand dryers. “I didn’t download a morality app.”

Spite is a sign of weakness. Using an extraordinary woman to put an ordinary one down smacks of spitefulness.

“Extraordinary?” Jack’s quizzical tone was genuine. He’d never heard Don give a compliment like that — at least, not when it was only the two of them talking.

Don shrugged. Above average, at least.

“You’re backpedalling,” Jack said, with a dawning realization. “You really like her. Don’t you?”

That’s not in my programming. Don put his hands in the pockets of his perfectly creased dress pants, scotch having mysteriously vanished. And you do, too.

“She might not even see us there,” Jack reasoned, feeling slightly guilty.

I’m just an advisor. It’s your call, Jack. Always is.

Alice’s reply shunted Don to a side window. She’d been wanting to try Nepalese cuisine for ages, and it was a shorter commute from the labs to boot.

That settled it.

On Thursday evening, Jack cranked out a dozen push-ups, exfoliated, showered, shaved, and dressed his best. He arrived at the Himalayan five minutes late, as recommended, but Alice looked far from nonplussed, sipping a white wine and listening indulgently to a young server stammering about specials. Jack’s stomach flip-flopped at the sight of her, but he managed to drag his eyes around the rest of the restaurant too, scanning for a familiar face, and then …

“Jack?”

He turned and saw her, the nose she’d drunkenly debated having straightened, the neckline of her dress over breasts he knew were slightly asymmetrical, the stubborn bit of weight clinging to her hips, and how beautiful she was stabbed him through the heart all over again. He barely noticed her date, some tall reedy type with hair razored fashionably around his cranial implant.

“Violet. This is a surprise.” Jack realized Don had stepped in.

“Yeah. Yes. Yes, it is.” Violet stared awkwardly back at her date. “Are you …?”

“I’m meeting someone,” Jack said for himself. “Already late. Sorry.”

Alice chose that moment to catch sight of him, giving a half-wave with one scolding, perfectly tweezed eyebrow raised. Violet followed his gaze.

“Oh!” Her cheeks flushed. “Oh.”

“Hope you have a great time,” Jack said smoothly, feeling a fierce sort of triumph. “I’ve heard the lentil curry is amazing.” He gave the tall man half a nod and made his way to the table he’d reserved. People were watching him again, but this time Violet was one of those people.

Jack barely tasted the roti, or followed the conversation, as dinner began. He was too busy catching glimpses of Violet’s date in the mirrored wall, and felt a small beat of satisfaction every time he caught her watching them. The words were coming out of his mouth in perfect algorithms and Alice was responding in all the right ways, sometimes playing with her hair, sometimes touching her beautiful neck. Don found a way to tangle Jack’s hand with hers, and after he leaned across and kissed her, he saw Violet reach for her coat. That meant he was only half paying attention when Alice sat forward, face serious.

“Jack, there’s something I have to disclose,” she said. “I’m not a real woman.”

That threw him, just for a second. He’d somewhat assumed her uncanny physical perfection had been helped along by cosmosurgery — wasn’t it always? — but her being transsexual hadn’t crossed his mind.

“Of course you are,” he said, because for some reason Don had no response. “I mean, self-identification is what makes us who we are, right? Not, uh, sex at birth.”

“You’re misunderstanding me.” Alice gave a not-quite-pained smile. “I’m a sapient escort doll prototype engaged in in-field beta testing. Legally, I’m required to inform you of that before any sexual relations take place.”

“Two glasses of wine and you turn into a comedian,” Jack said, desperately trying to channel Don’s calculated cool.

“It’s not a joke,” Alice said. “I’m a product of Fenderi Robotics. Alice 2.0. I really do like you, Jack. I hope this isn’t too upsetting.”

“I don’t think I believe you.”

Alice peeled back the skin of her hand to reveal a delicate tracery of circuits, and whatever reasonable explanation Jack had half-cooked in his mind promptly vanished. Fenderi. Small calibrations. He should have realized she was too perfect to be real.

His eyes darted back to the mirrored wall. Violet had vanished. With his stomach plunging, Jack scraped his chair back and stammered an apology. Alice inclined her beautiful head, as if she’d expected as much, and then Jack was tearing towards the exit. He caught her just as she and her date were climbing into an autotaxi together.

“Violet!”

She turned, still holding her date’s arm. “What, Jack?” Her voice was tired, confused, but mostly tired. “Why did you come here?”

Jack halted under the orange blur of the streetlamp, hands pocketed instinctively against the chill. He gave a helpless shrug. “I could say all the right things this time,” he said, though Don was still distant, still saying nothing.

“It wasn’t anything you said.” Violet’s date was opening his mouth, looking rightfully pissed, but she cut him off. “I told you that. It was just … dead, okay? You didn’t kill it. Neither of us did.” She shook her head. “Goodnight, Jack.”

Then she was gone, a trailing arm disappearing into the cab, then her lanky companion folding himself in after her, and then the autotaxi was pulling away into the darkened street. Jack crumpled against the streetlamp.

“Did you know?” he asked flatly.

Don finally winked back into view. I suspected.

“No wonder it was all so easy.”

It wasn’t. I could barely keep up with her. She’s fully sapient, Jack. And quite extraordinary.

“I probably don’t deserve her.”

Don adjusted his cufflink. What you deserve is some time. Maybe with a girl, maybe not. Maybe doing something for yourself. By yourself. He cocked a brow. It just takes time, Jack. I thought humans knew that by now.

“We know,” Jack said, taking one more look down the street. “It’s tough, is all.” He exhaled through pursed lips. Shook himself. “Maybe after I give it a couple weeks I can call to see if she’s still in beta. Just as a favour to you. Well. Mostly as a favour to you.”

Don raised his digital glass as Jack turned back to the restaurant, knowing almost exactly what to say.

Rich Larson lives in Edmonton, Alberta. His work has appeared in Word Riot, YARN, Prick of the Spindle, and The Claremont Review. His stories have appeared thrice previously in AE.