CupidAI by Cotton O'Connell

A new AI trained on intimate personal data matches an odd couple, who must navigate their way through an awkward first date.

Image generated with OpenAI
A man and woman are having dinner together for the first time in a Peruvian restaurant. She sips sangria and eats a ceviche appetizer, and he tries to catch the waitress's eye to order a second beer. The restaurant is upscale and overpriced - not what she would have chosen for a first date, but this was his pick. They've already ordered a rotisserie chicken to share as their main.

"So what do you do for work?" she asks to break a pause that was getting uncomfortable. Until now, they had kept to small talk, pinpointing where the other one lived in the city via nearby restaurants and landmarks and giving the menu unnecessary scrutiny. "It's weird how this works, that we don't know anything about each other. If you told me five years ago I'd agree to this, I'd never have believed it."

"Yeah, the app doesn't have profiles because the founders think they lead to preconceived notions," he says. "About the other person's intelligence and how much money they make and things like that. People also tend to lie on their profiles, but that's a different problem." He seems more relaxed as he slips into a didactic tone. She takes note of this. A potential red flag.

"I'm a tech journalist," he continues, and he tells her the name of the publication he writes for and feigns unconcern that she hasn't heard of it. "I usually cover the major platforms, the Googles and Amazons and Apples, but I did a story on CupidAI recently and interviewed the founders. So that's why I'm able to repeat all their talking points."

She notes the self-deprecation and approves of it, so long as it's not emblematic of a deeper personality flaw. She's trying to break her pattern of falling for overconfident men who inevitably end up cheating on her, dumping her, or simply thinking they're better than her, but at the same time she fundamentally can't be attracted to someone with low self-esteem.

"This isn't research for one of your articles, is it?" she asks. She sounds more accusatory than she had intended as she gestures back and forth between them.

"No, definitely not. They offered to let me into the beta after the story posted, and I figured, why not? I would never violate your privacy. Unless, of course, this went really well and you agreed to be part of a future story."

He blushes and wishes he had another drink, but the server is ignoring him, maybe on purpose. He's not sure why he said something so earnest and cringy. Normally this only happens with really attractive girls who are out of his league. This woman is nice-looking enough, with warm brown eyes, and perfect teeth out of a toothpaste commercial, but too old. His best guess is thirty-five, but of course the app doesn't give that information. Dating her would mean an immediate conversation setting a timeline for marriage and babies, which he has no interest in. At twenty-nine, as an average-looking guy with an average job, he should finally be hitting his prime with single women his age who are getting a bit less picky or girls freshly out of college who want to date older men. Not that her age is disqualifying, or her race, though he's never been romantic with a Black woman before. Maybe it's this, the possibility of coming off racist if he's not interested in this particular match, that's making him nervous.

"No worries," she says, registering his embarrassment. How refreshing it is to be the person on the date who cares less about the impression they're making. She was positive this would be a dud from the moment she saw him - with the identifying Cupid's Arrow pin they were both told to wear on his fleece. (The app didn't provide pictures, just told them each other's first names and opened a text chat to let them arrange a time and meeting place.) He's too young, too ill at ease. Most likely a tech bro whose smugness will curdle into petulance when she remains unimpressed by him. She's met the type before.

She's starting to hope for an epic fail to entertain her married friends with, though she normally resents their interest in her dating life. It would prove what she already knew before she agreed to try this (out of desperation perhaps, but also because she liked the idea of being an early adopter of norm-shattering new technology): that what she's in search of can't be inferred by algorithms, no matter how many MIT and Caltech pedigrees are behind them.

"Do you know how the matching works?" she asks, lobbing him a question she knows he'll like, but making it abstract to avoid consideration of how the two of them were put together. "I know we had to give the app access to our phones. That was a tough call for me. But my friend from college is their head of finance, and he convinced me it was above board and I could sue the shit out of them if it wasn't."

"It's kind of a black box," he says, feeling emboldened now that he's finally caught the waitress's eye and gotten his drink order in. A Manhattan instead of a beer to help him relax; he still has no idea why he's so worked up. "Once you opt in, they analyze all your behavioral data - links you click on, articles you read, posts you hover over - to understand your real interests, which might be different from what you'd put in a dating profile. For example, I play a lot of video games, but I don't admit that on other apps. I put down things like cycling, snowboarding, and volunteering at the animal shelter as my hobbies, and they are, kind of, but not as much as video games. Do you play video games?"

"No," she says.

"Just curious. Anyway, tracking people's online activity is just table stakes, no different really from what Google and Facebook do to sell ads. The algorithm gets a way more detailed view of who we are by analyzing our texts and emails. Then it uses what it's learned, those hidden signals in our writing, to create matches based on its training data."

"What sort of training data?" she asks.

"They've analyzed conversations between long-term couples. In order to find patterns in communication styles that help predict compatibility," he says. He suspects she won't like this answer, since a lot of people don't. It's the reason his CupidAI story went viral. He personally sees nothing wrong with this so-called surveillance, since the couples were paid handsomely out of a trove of venture capital funding. The way he sees it, there are far more degrading, less lucrative ways to earn money.

"Wait, you're saying they fed their algorithm with people's intimate conversations? That's incredibly creepy," she says, right on cue. He's surprised she didn't know this, especially after she mentioned knowing Cupid's finance chief. He guesses that person is more like an acquaintance than a friend. She seems like the sort to name-drop.

"People opted in and got paid," he says with a shrug. "It's not like the researchers were planting secret recording devices. And that's really all I know about the matching. Not even the founders could tell you exactly how it works."

The server arrives with their chicken, served with yuca fries on the side, and his Manhattan. She surprises herself by ordering another sangria even though she isn't quite finished with the one she has. She's not usually much of a drinker but feels pleasantly buzzed and wants to keep it going. Contrary to her expectations, she's enjoying this. Not so much him - he's turning out to be puffed up with false confidence, as she suspected - but the puzzle of why they were matched. She's always loved puzzles.

"So I want to figure it out," she says after swallowing her first bite of chicken, which is tender and delicious. "Why they put us together, I mean. I want to break the code."

"Okay," he says, drawn in by her enthusiasm in spite of himself. She even looks a bit different now, all lit up with positive energy, her Resting Bitch Face softened. He has to admit she's pretty, with a heart-shaped face, which he never knew was a real thing. "How should we go about doing that?"

"I'd say we start with the basics, the stuff that normally goes in a dating app profile. It wouldn't surprise me if the founders raised all that money by pretending to create a superintelligence they barely understand, when really it's as simple as pairing off dog owners or people who like Game of Thrones. My guess is it's not nearly as sophisticated as what they told you," she says archly.

She's now poked one of his most sensitive spots, causing his unsettled feelings about her to veer suddenly into dislike. He's highly attuned to the critique of tech reporters covering their subjects too rapturously - a critique he largely agrees with, but doesn't think applies to him. He thinks it's possible to be skeptical without being a skeptic, and he looks down on colleagues whose stories automatically focus on negative implications and worst-case scenarios without expressing a sense of wonder when tech actually delivers on its hype.

He takes a beat to compose himself before responding. His last girlfriend, who dumped him two years ago, accused him of being a Mansplainer, and though he didn't take any of her grievances seriously at first, he came around to see what she was saying. He knows about his tendency to flex superior knowledge in uncomfortable social situations (though he would argue not just with women) and that it wouldn't go over well now. And while he agrees that the algorithm has failed today (which she hasn't said outright but doesn't have to), he doesn't want open hostility. All he wants is to spend the next forty minutes peacefully, then be freed into the cool spring air.

So instead of saying her proposed experiment is silly, he decides to play along. "Alright, I'm game to try. I'm twenty-nine. From Newton, Mass, originally. Two sisters (I'm the middle child). Parents are accountants. Went to UMass for college. English major. I have a feeling you think that's a dumb thing to major in? You're in finance, right? Or law? I covered local news for a community paper for a while after graduating. Then moved across the country for this job. Hobbies, as you know, are outdoorsy, sporty things and sporadic volunteering, but really video games. I also read a lot, sci-fi mostly, but I wouldn't put that in a dating profile." His index finger taps out a frenetic rhythm on the table as he considers whether to be satisfied with this account of himself. "Your turn."

His deadpan delivery is funny, but she doesn't laugh since she can't tell whether it was intentional. She senses from the way he breaks eye contact once he's done speaking that he's working to suppress some irritation. This isn't anything new to her - being off-putting to men when she lets herself be sarcastic or even just unfiltered in her thinking. But it usually occurs in a work setting. On a first date, she normally tries to be as unobjectionable and broadly palatable as possible, but there was no way to keep her face neutral when he was nonchalant about a tech company eavesdropping on people. (She had already known about the "training data," as he put it, from reading up on Cupid before agreeing to join the beta, but his cavalier way of describing it made her want to distance herself - from the concept and him.)

It was one thing to participate in something ethically questionable with reservations, as she was doing. Quite another to have zero qualms about it. The former made you a normal, flawed human, while the latter seemed deeply problematic to her.

In response to her uncontrolled facial expressions, she had expected him to double down and keep enlightening her on the ins and outs of "black box" platforms and training data. She gives him a little credit for presumably letting that impulse slide.

"My turn, okay, let's see. I'm thirty-six, and I appreciate the way you're trying not to react when I say that. I'm surprised they would match us, with our age gap. We must have an awful lot of shared interests. Or maybe a rare secret fetish." He blushes instantly, as if he were a toy and she had pressed a button to trigger this reaction. She can't help but laugh, as though someone had also pushed a button on her.

"You don't have to say anything about how age is just a number and you only see the person. Please don't, in fact," she adds, getting her laughter under control. He smiles pleasantly, with no animosity. She gives him credit for that, too.

"So I'm from Jersey. Went to Rutgers, then Columbia Law. Yes, I'm a lawyer, but I was also an English major in undergrad, so I don't find it dumb at all. Went to a huge meat grinder type of law firm in New York after graduation. Worked insane hours and hated it. Got to pay off my student debts, at least. Switched to in-house counsel at a bank for less pay but better hours. Met someone there who I thought I would marry. Broke up and everything reminded me of him - my apartment, our gym, the office obviously, the dry cleaner where I picked up his suits, the restaurants and bars we liked. Even places we never went to together, because I remembered talking about him there, or even just thinking about him. Wanted a change. Applied for a job at Google, and here I am, two years later, in San Francisco. Hashtag living the dream. Do people say hashtag anymore? I'm usually a few years behind."

"No," he laughs, "not really."

"Figures," she says.

It's odd to talk about Jon, though she thinks about him every day. The rawness of her feelings about their five-month relationship is usually a private humiliation. She's too embarrassed to talk about him anymore, not even with close friends, who must assume she got over him ages ago. It's lucky that Jon's social media presence is confined to LinkedIn, where he looks preppy and overzealous in his application of hair gel in the same unflattering photo he's always used. There's no way of keeping tabs on his perfect girlfriend, then fiancée, then wife, with the perfect baby bump, living in the perfect McMansion in the perfect New York City suburb. Still, in her bones, she knows these unconfirmed facts about his life to be true.

It wasn't the duration of her time with Jon that mattered, but what she had told herself: that he felt exactly as she did. She's combed through her memories to find the signs she was deluding herself, that he was telegraphing ambivalence all along, but they weren't there, these signs, until the end.

"Any hobbies or interests worth sharing, or are you a hundred percent about working?" he asks. She can tell he's trying to lighten the mood, whether out of consideration for her feelings or his own, it's unclear, but it works. She stops studying the dipping sauces for the yuca fries and meets his eyes again.

"Sure. I've loved running since high school. It's how I've gotten to know the city here. It's so much smaller in every way than New York, which is good and bad. Mostly bad, if I'm being real. I love reading fiction - not sci-fi, sorry. What else? I do watch TV, but none of that heavy, prestige shit. I love the Real Housewives and baking shows and Queer Eye. I've pretended to like Ted Lasso on so many first dates, but I don't even know what it's about. I feel like I should be honest with you so we can get to the bottom of this thing. Also, how are you not asking about my secret fetish? I gave you a perfect opening when I was speculating about why the Cupid overlords matched us."

His cheeks burn again as he catches a triumphant look on her face. Is she flirting with him? Or just messing with him? It's unclear, but he doesn't care. He realizes that, in a way, this is becoming the best date he's been on in months, which isn't to say he's changed his mind about her. She's full of herself and emotionally unregulated, but unpredictable unlike most of the twenty-four-year-old women he meets on Tinder, who talk about Coachella plans and how their semester abroad in college shaped their worldview and British Royal Family conspiracy theories and other drivel. To be fair, he's usually only interested in hooking up with these women anyway, succeeding with about thirty percent about them. (Not a great rate, but improving as he gets older.) But tonight is fun, even with a limited prospect of sex. Her fetish references remind him of a precocious child trying to shock an adult family member with a blue phrase she's learned, not indicative of real intent.

The waitress comes to check on them, and they both order another drink. She knows she'll be drunk but doesn't care. She takes a good look at him as he gets up to use the bathroom and decides he looks like an adult version of Harry Potter, but taller. He even wears similar glasses. It's oddly appealing, though she tends to like guys with muscle tone, who look like they work out, because they do. He's not her type physically, this much is clear. She wonders if she'll end up sleeping with him, if all the drinking she's doing is really for liquid courage.

He returns looking pleased with himself.

"I was thinking we could ask each other icebreaker questions, like you see on some of the apps," he says. "To help get deeper than the boilerplate, job interview-type of info we've been sharing. Or I've been sharing anyway. You opened up a bit more." He stammers, worried about being too on the nose. He felt for her when she mentioned her previous relationship, though he's never known that type of pain, not in great depth, or for long. He was upset when his ex-girlfriend dumped him, but it passed.

"I was thinking something like 'two truths and a lie' or 'the craziest thing I've ever done,'" he adds. "What do you think?"

"I'm up for it. Two truths and a lie is perfect, but you first." She takes the opportunity to study him more closely while he figures out what to say. She can see, now that he's taken off his fleece with the Cupid pin, that his T-shirt is perfectly too tight, showcasing more developed biceps than she was expecting for a guy so lean. Now that she thinks about it, it's been seven months since she last had sex, which explains these thirsty feelings. Not that that occasion, with an advertising executive who pounded away for three minutes, mostly oblivious to her, even really counts.

"How's it going over there?" she asks.

"Don't rush me, I've got to get this right," he says. She hadn't registered before that she likes his voice, which is deep and melodious and sounds like it belongs to a more substantial person than she initially took him for. "The stakes are awfully high here. If we don't find a way to flush out what the algorithm saw between the two of us, we might not bother to actually fall in love." She wonders if he's flirting with her, but his seriousness makes him hard to read.

"Okay, here goes," he says. "I have a seventeen-year-old Siamese cat named Pilar who sleeps in my bed with me. I've traveled to over thirty countries. I had a nervous breakdown in college."

"Hmm," she says, holding eye contact while she thinks. "Traveling to thirty countries is the lie because it's generic. You might expect me to think it's true, so it's a red herring. The other two are more specific and personal. How did I do?"

"You're right." He lifts his Manhattan in a pretend toast.

"Do you want to say anything else about the truths?"

"Sure, I'll talk about Pilar all day. She's my best friend. I've had her since I was a kid, and she hates everyone except me. The other one? Maybe not the best content for a first date, even with my algorithmic soulmate, but let's just say I had parents with very high expectations, and I consistently failed to meet those expectations from a young age. Eventually, the chickens came home to roost."

"Do you talk to them?"

"Sure, I do. They're my parents. Enough procrastinating, it's your turn."

She's participated in enough corporate team-building exercises to have a pat answer to versions of this prompt. When a little known fact about her is required, she normally confesses to sneaking into the pantry of her childhood home and drinking vinegar from the bottle. It's the perfect quirky answer because it's not revealing. It's not even true; she made it up years ago, in law school. But today she wants to challenge herself.

"Okay, I'm ready. I'm thinking seriously about quitting my job and becoming a cardio kickboxing instructor. I've had two abortions. I go to church."

"The last one is the lie," he says immediately. She draws out the suspense for a few seconds.

"No, the first. I knew you'd fall for it because everyone thinks lawyers are miserable, but I enjoy my work. I went to Catholic school all the way through high school even though my parents aren't religious, but it was a really good school. I never wanted to set foot in a church again after graduation, but I got lonely after I moved to SF. I didn't know many people here, so I started going to mass on the weekends. There's a nice little community there, mostly older folks, immigrants, families with young kids. As for the abortions, we don't have to get into those, but I was really young, and thank god for them."

"Well played," he says, disgusted with himself for being aroused. He's in a suggestible state, with a short pathway to arousal, and the thought of her having an abortion led naturally and inevitably to the thought of her having sex.

The server comes with the dessert menu, which they decline, since neither is a dessert person - a fact they both quietly seize on as common ground. A busboy clears their plates. Suddenly neither of them can think of what to say or how to build on their gains. They both consider introducing another icebreaker question but decide it seems desperate.

They nurse what's left of their drinks and ask general questions about each other's lives, which is familiarly effortful and depressing for both. He talks about the kind of news he likes covering, and she talks about the area of law she practices. They describe recent travel and ask perfunctory follow-up questions. It reminds him - the unoriginality of these questions, the sudden pointlessness of it all - of the time he stood in a richly imagined room on the set of a TV show in LA with a screenwriter friend who was giving him a tour. A crew arrived to break it down with horrible efficiency, and the paintings and dishware and carpets that had looked so real were unmasked as props. It was unsettling to watch.

She reaches into her bag to check her phone. It's already a quarter to ten, and her preferred bedtime is in fifteen minutes. She's always been a morning person, and everything about this guy reads night owl. He's probably up until one or two in the morning, reading arcane Reddit threads with his cat in his lap, and getting up at nine because all the people he deals with for his job operate the same way.

This is not her person, she's sure of it. But after so many years of trying to make careful, deliberate choices, it's tempting to live in the haphazard way other people do - wearing athleisure to work, sending emails without editing them for tone first, drifting toward someone not because they're right, but because they're right there, and an algorithm told you to. It's a privileged way of moving through the world that's never seemed open to her.

He catches her peeking at her phone and wonders if he said something to make her so vague and distracted. For a moment, it seemed they had something electric and out of the ordinary, but it vanished as quickly as it sparked, like a firefly dropped in a jar made of vapor.

The truth is he had hoped to feel a connection tonight, even a low-voltage one. Given the limited pool of female beta users on the app, he hadn't expected the match to be perfect, but he still wanted a taste of magic. Which is why he felt let down - betrayed even, after the in-depth, ultimately favorable article he had written about Cupid - when it seemed clear within the first five minutes of meeting her that the app had it wrong.

It wasn't that he was expecting someone clearly his physical type. He had been braced for Cupid's reasoning to be based on inscrutable, spiritual parameters, given the early success stories they had touted, which included a professor of ancient Greek falling for a Verizon store manager, and a sculptor known for provocative works falling for a Fortune 500 company CPA.

He had been open to the idea of the algorithm knowing him better than he knew himself. If she had seemed wildly off the mark, he might have reserved judgment, waiting for the brilliance of the methodology to reveal itself, but she was too close on paper to someone he'd pick for himself. (The fact that she was older and darker-skinned than women he normally swiped right on felt like a cheap trick, as if he were being tested.) She was off by just a few clicks - a little too strident, a little too cocky, a little too perceptive - but enough to throw the efficacy of the whole project into doubt.

Then they had gotten a bit drunker and looser, and he changed his mind. He had thought about taking her home, undressing her slowly, and finding out more of her secrets. She had seemed like a place worth getting lost in, practically more of a destination than a person. But they had tripped somewhere, and the walls had gone back up.

With the restaurant almost empty now except for a few desultory drinkers watching the Giants game at the bar, a colder reality had set in. The server arrives with their check, and he grabs it, inserts his card into the little plastic sleeve without looking at the total, and hands it over. He's decided he wants to cut to the awkward goodbye and get out of here.

As they wait for the server to release them back into the world, she finds she has nothing to say and starts to panic. She searches her mind for a single pleasantry and can't recall whether she even thanked him for buying dinner. He's fully immersed in his phone now, giving her cover to do the same. She scans her work emails. Nothing urgent. She can already picture herself saying "It was nice to meet you," then turning the corner to hail a Lyft in order to avoid more uncomfortable chat while they wait for separate cars. Her disappointment is unexpectedly dense and smothering. The waitress arrives with the receipt. He signs hurriedly.

They stand and get ready to leave. She slips on a belted trench coat that reminds him of what a femme fatale character from a noir movie might wear, solidifying an idea he's been having that she belongs to another time. Then she pulls the Cupid pin out of her lapel and slips it into her pocket, not discreetly enough to go unnoticed.

He puts his fleece back on, and she notices something she hadn't seen before: a small tattoo of an elephant in black ink on the underside of his forearm near the elbow. It sends her back to a summer almost twenty years ago on the Jersey Shore, when a college friend who seemed much too beautiful and effortlessly cool to be invested in their friendship had wanted to get tattoos together. The friend helped her choose an elephant, but she had chickened out at the last minute. Their friendship outlasted the summer, but not by much.

"So what do you think?" she asks once the restaurant door has swung shut behind them. "Is the app smarter than we are?"

He was expecting her to deliver something like this - some summation of the evening, perhaps a sarcastic one. But her tone is nervous and soft. He takes her hand without thinking. They have the block to themselves, and it feels like the city is already asleep.

"Maybe," he says. "I was hoping it was, but I'm honestly not sure."

She takes a step closer. Her nearness lets him take stock of her long eyelashes and high cheekbones and amazing smell - a mix of lavender and citrus, with a note of something earthy, like pine needles. Her hold on his hand tightens, then relaxes as if she's about to let go. He's relieved when she doesn't.

"I don't know about you, but I think I'm willing to believe it might know something I don't for a bit longer," she says after a pause.

It seems like the right moment to lean in and kiss her, but he hesitates. The spectrum of emotions playing out on her face makes him think of the spinning wheel of a game show, hurtling recklessly past any number of possible outcomes.

He inches closer, which makes that expressive face of hers turn into a pretty blur, and breathes her in. "For now, maybe we can say we need more time to crack the code. Figure out how the whole thing works. We need more data, don't you think?"

"We do," she says and tightens her grip again.

It's decided that he'll come back to her apartment, and she hails a Lyft. She wonders if he agrees to it - her place, not his - so readily because of his roommates and unwashed sheets and cat hair-covered furniture. He wonders if this is more trouble than it's worth, if he'll be sorry tomorrow, though he isn't in the habit of regretting things. They stand at the curb waiting for their car, and she whispers "Brrrr" and leans into him even though it isn't particularly cold.

He puts his arm around her and they wait. It rests stiffly on her shoulder at first but gradually softens, like a stick of butter thawing.


  1. Great writing - so layered and clever. It's obviously a story about technology and a date, but beyond that it's so much more - the life stories of two lonely people, people who are perhaps a little tired and cynical, coming to a point where they just might be finding love. So, this story is a very modern dating tale, but also a genuinely well told love story. Great work.

  2. I can see why this is the pick of the month. I felt completely invested in the journey as we switched between their thoughts. It was very clever as well. Just the see-saw between positive and negative assessments. I love the narrative voice. Fantastic story!

  3. This story is fantastic. I was hooked at the start and all the way to the end. I enjoyed the characters; they had great depth to them, and I was engaged and curious about the outcome of their fancy-AI-matched date.

  4. I very much enjoyed this fiction. It had terrific metaphors, foremost among them the final one: “He puts his arm around her and they wait. It rests stiffly on her shoulder at first but gradually softens, like a stick of butter thawing.” Although we learn a lot of the backstory of the MCs, we are yet kept at arm’s length by not learning their names. A very effective literary device. They are everyman and everywoman, experiencing many things in their lives that we can all relate to. It’s amusing, the way they talk them in and out of sparking an interest in the other. In the end, they are just two lonely people. A poignant, quality story. Thanks, Cotton, for both writing and sharing.

  5. This is a wonderful story told with such skill in the challenging third person omniscient point of view.

    We readers are left to wonder… What is the true nature of CupidAI?
    (For me - my grand reveal would be that the company is a sham and the “AI” is actually just a randomizer program!)

  6. Elderly male here who never dated much is amazed by the internal machinations of two algorithm matched daters. I'm not surprised that the algorithm seems smarted than the daters. So much of our lives happens unconsciously.

  7. Really enjoyed this one. Reminded me a bit of the happen, but was one of the possible permutations the dating AI had foreseen. Yet this story felt more real. The female character was particularly vivid. Great stuff!

  8. I enjoyed reading about these two characters. They are like two icebergs colliding. They only see each other’s tips, but their pasts, desires, dreams and fears lie under the water. Well done, Cotton!