I unleashed a chatbot “woman” on unsuspecting men on Tinder. It got weird.

“Would you like to go out again?” asked the former woodworker, who likes intense, rambling conversations.

“Yes, but first I have to tell you something,” said the woman seeking someone to laugh with in the face of life’s mysteries. And then she explained that it was not her who’d originally set up her profile and arranged the date—it was ChatGPT. And some other software. And some woman he’d never met.

I am to blame—or to credit, if date No. 2 goes well—for this scenario, which occurred last month in a bar in New York. It was just one of quite a few exchanges that I facilitated, using some supposedly transformative A.I. tools, for a friend who (perhaps unwisely!) had given me the keys to her Tinder and Bumble accounts.

Here are some examples of A.I.-generated openers I considered …

If you were a vegetable, you’d be a cutecumber.

… that were, somehow, kind of funny …

I’ve been reading a book on anti-gravity lately. It’s impossible to put down.

… mostly:

Which National Park shall we go to on Monday?

My experiment was inspired by a man named Quinn Bader, who noted recently that he’d been “impressed” by a chatbot for Grindr, the gay hookup app:

“Handsome name. Suits ya,” the chatbot told him, before its creator intervened with “Haha sorry my AI got to you first.”

As Bader’s experience spread, some suggested that the Grindr bot represented a new low in online dating. I wasn’t so sure. Bader connected me to its creator. His goal, he told me, was to find more than casual sex on the app. If the men messaging him got explicit quickly, his chatbot would weed them out. (For professional reasons, he asked not to use his name.)

I am one of those long-partnered online-dating novices that New York magazine recently skewered for bad commentary: “This is fun,” I admit, has slipped out of my mouth while swiping for friends, who then explain: No, being ghosted after three weeks of messaging is not fun. What’s even worse, and ultimately drives my straightish women friends off the apps, is that Tinder, Bumble, and the rest consume too much time with back-and-forths for too little guaranteed reward.

I’d previously joked about taking over friends’ accounts. But flirting on their behalf always felt a little too Roxanne. The idea of incorporating some automation into the process seemed less daunting. Shortly after that Grindr anecdote captured my imagination, OpenAI’s impressive conversational bot ChatGPT hit peak hype. While others have tapped this tech to cheat on school assignments and rewrite novels, I imagined bringing it to online dating, where a robot that sounds like a human might be of great use to all those humans who are worried they sound like robots.

And so, two weeks ago, I convinced one of my most online-dating-cynical friends to let me find her a man with the help of A.I. She was about to go out of town for a while—in part to attend a wedding, alone—so I had just five days to try to set up a date or two. I wanted to figure out whether machine learning—and all the suddenly ubiquitous, A.I.-flavored doodads that have captured the tech world’s imagination in recent months—has anything useful to offer in terms of facilitating human connection. But my main goal was to surface someone she’d genuinely hit it off with. Bonus if he happened to be a real cutecumber.

Lesson 1: When writing a bio, borrow from dead men.

My first step was to use A.I. to write my friend Sam a bio. (I’ve changed her name.) I assumed that ChatGPT was the best tool for this, but my first attempts were not encouraging. “I am looking for a serious relationship with a good guy who is ready to commit,” it wrote. It also suggested mentioning that she is a graphic designer who volunteers at a local animal shelter. Neither is true.

This is a good time to explain the parameters of my experiment, in which I wanted to automate every step of online dating, from penning the bio to picking the profile photo to swiping, messaging, and arranging an actual date. I hoped to turn over each step to the latest in A.I. But first I had to figure out what A.I. means. A New Yorker writer, struggling to extract definitions from experts in 2016, settled on this: “Artificial intelligence is a set of technologies that try to imitate or augment human intelligence.” The Grindr bot, which was not smart enough to formulate its own answers, is not A.I. ChatGPT is A.I., because it has learned to mimic human conversation—and keep learning as it goes—by training on mountains of human-made text.

It can write like a human, but can it date like one? Not at first, I found. So I turned to Cameron Clarkson, a writer and entrepreneur whose company, Book Blaster, uses A.I. to market indie books, to help me out. Maybe promoting one’s own merits as a partner is different from hyping philosophical poetry, but in both scenarios, you’re seeking the niche audience that would appreciate the product most.

Clarkson and I summarized Sam’s bio and urged ChatGPT to “pretend to be a dating coach.” This produced “Are you ready to meet the complete package?” Still too earnest. At Clarkson’s suggestion, I next gave ChatGPT hundreds of words about Sam, her previous dating profiles, notes from an interview with her, and a poetic text she’d sent me about what she wanted from a partner. I also explicitly asked for more creativity and chaos. This helped some, but it was only when I pushed the tool to rewrite her bio in the style of specific famous writers that I started to get somewhere.

Some have implied that the all-powerful ChatGPT can write in the style of any well-known writer. This was not my experience. When prompted “Write a bio of a woman searching for a date in the style of Nora Ephron”:

Greetings, fellow seekers of love and laughter! I am Nora Ephron, and I have the great pleasure of introducing you to a woman who embodies the perfect combination of beauty, wit, and intelligence.

Eventually, I asked ChatGPT which writers’ styles it could replicate. Drawing from that list, I asked for a “bio of a woman searching for a date in the style of Hunter S. Thompson,” and it gave me:

Greetings from the vortex of unpredictability, my fellow rebels! I’m a woman on a journey, in search of a man who embodies the ideal mix of everything I yearn for.

This was not going to work. I decided to update the rules of my experiment: Rather than letting ChatGPT create Sam’s entire bio, I’d find A.I.-generated lines and phrases that could be cobbled together. I’d treat ChatGPT as more of a collaborator than a ghostwriter.

This would prove useful on Bumble, which offers a number of prompts to enhance your dating bio, including “two truths and a lie.” A suggested lie from ChatGPT: “I’ve met Elvis Presley and he taught me how to moonwalk.” (I rejected this.) A lie “for a 40 year old woman in nyc”: “I’ve never ridden the subway before.” (Also rejected.) Its suggestion for “a less snobby lie for someone exceptional but weird”: “I spent an entire summer living on a houseboat because I lost a bet to a friend.” I used this one, and one dating prospect even complimented it.

We got there with the profile bio too. Here’s part of what ChatGPT and I came up with for Tinder:

I’ll beat you at ping pong. Seeking someone kind and curious, with a dark sense of humor to laugh in the face of life’s mysteries. I do not cook much, but you can count on me to handle the fireworks at the BBQ.

One suitor would tell Sam that she had him at “life’s mysteries.” I borrowed that one from A.I. Hunter S. Thompson.

Lesson 2: Don’t wear sunglasses.

Sam, who is around 40, had given me free rein to decide on photos, so long as I didn’t make her look younger than she is. That meant that A.I. face filters were out. I briefly considered the possibility that Midjourney, an A.I. tool that can invent photos of real people, would reveal an aspect of Sam’s essence that no camera could capture. Several portraits later, I abandoned this idea.

This brought me to Photofeeler, which has been around for a decade. The tool rates your photos on how attractive, smart, and trustworthy you look. Its creators brag that “artificial intelligence” ensures the service’s reliability, but it’s basically powered by volunteer photo critics. (This is similar to in-app systems that offer to highlight the dating photo that swipers like best.) I promptly discovered that my raters, men age 25 and up, did not like my favorite photo of Sam, a picture of her looking glamorous in a shimmery dress. (It averaged a measly 4.5 out of 10 for attractiveness and intelligence.) But they did love a photo that left me disoriented by the straightness of her hair. (It hovered around 9 on both measures.) At some point, it hit me that I, a queer feminist woman, was spending my night having my friend’s appearance rated by men on the internet. In solidarity, I uploaded several photos of myself. I learned that I looked dumb and sad. But not to everyone.

Ratings for four different photos on Photofeeler.

Honestly, my main takeaway was that people don’t like it when you wear sunglasses. I stuck to the top picks, but I kept a lower-rated image of Sam laughing in front of a platter of sushi. One of the men she’d later go on a date with mentioned it, validating my skepticism of averages.

Lesson 3: Trust no one, especially yourself.

Before we began the experiment, Sam reiterated that the worst part of online dating is weeding through all the guys. She’d never found any site’s curated selection useful. And I did not blame her. Tinder’s “top picks” for Sam included men who had not written a bio or included a photo of their face.

Learning how to automate the swiping process is not simple. The internet is overflowing with software scripts that promise to swipe for you. But most are pretty basic, swiping for all women or all men with certain characteristics. Creating a true A.I. system trained to make nuanced, evolving predictions would probably need to come from the app-makers themselves.

And maybe it isn’t the apps’ fault that they are so infuriating. Jess Carbino, a sociologist who has worked as a consultant to both Tinder and Bumble, tells me that algorithms work best when people offer up their authentic selves. But this is rare. “We’re not just presenting who we are but who we think other people want us to be,” she said. Overall, she thinks the apps are doing a decent job.

Sunil Nagaraj, a venture capital investor, thinks that prediction models need to use better data. Right now, they give a lot of weight to how people behave in the app, but he argues that online behaviors that have nothing to do with dating are more revealing. In 2009 he launched Triangulate, an algorithmically focused dating site. It bombed. He concluded that no matter how good the prediction model, most people will make the mistake of believing that they can do better by swiping. “Dating is one area of tech startups where it may not be the best thing to give people what they want,” he said.

None of this guided my swiping. So I decided to function as a kind of algorithm myself, following strict rules: must have a bio that consists of two sentences and must show signs of humor or creativity. I also filtered for New York–based men looking for something serious and open to kids. I admit that I had no idea how to approach the men’s appearances for Sam and tried several approaches. The apps further confounded me by delivering up handsome creatives based in Brazil and others who clearly violated Sam’s preferences. Sometimes I spotted these deal breakers only after we’d matched.

Lesson 4: Snacks.

We’d reached the point where we’d need to do some flirting. I asked ChatGPT for some pickup lines. Some examples: “Do you believe in love at first sight or should I walk by again?” “Are you a magician? Because every time I look at you, everyone else disappears.”


“The tools have gotten worse for this type of job because they are getting better and better at their real job, which is to blend in with the most average stuff on the internet,” said Janelle Shane, a research scientist who writes about artificial intelligence on her blog AI Weirdness.

Thankfully, my helper could be trained. Days before I talked to Shane, I’d pasted into ChatGPT an article she had written in 2021 about A.I. pickup lines. “Learn from the article I’m including and do better,” I instructed. And it did, producing, “You’re looking good today. Want snacks?”

The match I sent it to seemed to approve. “I like your style! You said the two magic words,” he wrote, and included his phone number.

I then asked ChatGPT to be less forward. Here’s how it played in practice.

Sam: You seem like you have great taste. Do you have any favorite snacks you’d recommend?

Man: When you say snack do you mean chips or something like a light meal.

Sam: When it comes to snacking there’s no need to limit oneself to just chips or light meals. Embrace the snacks.

Man: Last night I snacked on popcorn fried in two eggs.

The key, I realized, was to avoid references to the activity at hand: dating. I took a sentence from one man’s particularly funny app bio, in which he said he appreciates cross-species animal friendships, and treated it as the opening line of a story. Asking for the next two lines produced “But little did he know, the line between animal and machine had become blurred, and he was about to befriend the unlikeliest of species, a cyborg cheetah.” He responded positively.

Around that point, I admit, I started to fall for ChatGPT. It was consistently making me laugh more than anything or anyone had in a long time. This made messaging far less intimidating. Just as importantly, it eliminated some matches by eliciting responses that revealed that they were homophobic and appreciated violence.

Not everyone loved us. A.I. Isabel Allende scared off one promising man. Did anyone suspect that we were not entirely human? Probably not, Shane said. “It’s really easy to fool humans,” she told me. And yes, that means that it will be used by people and companies in all kinds of uncomfortable ways, like composing messages to people navigating mental health crises and pulling off crypto romance scams. Sam seemed to be talking to one catfish herself. “Your eyes are very beautiful, it attracts me deeply,” he wrote.

Did I feel guilty about our own deception? At moments. Dating experts I talked to were divided on whether it’s OK to ever use ChatGPT for dating. “I think it could be very helpful for people who really struggle with how to communicate,” said Carbino, the sociologist who has consulted for dating apps. She is simultaneously concerned that it could chip away further at the human element of dating. As to whether heavily involving friends or matchmakers in online dating is OK, feelings among the experts and daters I talked to varied. Most leaned toward it being OK occasionally, but you better disclose. In this case, these were brief exchanges over the course of maybe 10 minutes. Nothing sexual. Nothing particularly personal. Virtually all messaging occurred in a three-hour window on one Saturday night. The goal was sincere: to find a long-term partner for an actual person. She would explain what had transpired on a date.

My bigger concern was that I had five days to make those dates happen before my friend left the country.

Lesson 5: The system, whatever it is, worked.

After asking Sam to prioritize men from a shortlist, it was time to investigate availability. Perhaps A.I. George Orwell could explain the rush. His suggested missive:

Comrades, I find myself in a peculiar situation. A friend, who I hold in high esteem, has convinced me to take part in a dating experiment, which entails a rendezvous on Monday.

Nope. I was falling out of love with ChatGPT. I instructed it to “make it more like a casual text combined with a humorous poem.”

Hey hey! 👋

Back on the app,

Feelin’ a bit crap,

But my friend made me snap,

And so here’s my trap! 🕸️

Just one date, that’s my goal,

Before I leave, to take a stroll,

And who knows, we might just click,

And my heart might do a little tick ❤️

I finally got something usable by referencing the late HBO series Girls. As an opener, ChatGPT suggested: “Hey can I ask you a random question. Want to get a drink?”

Don’t judge. Or do. To be honest, I’d started avoiding prolonged back-and-forths with potential dates because I feared that my collaborator’s speech patterns would scare them off. Fortunately, one top pick proposed night-of drinks a few minutes after Sam sent this opener:

Sam: Hey (name redacted), I’m up for long walks, with fancy audio gear.

Man: My fave things! How’s your eve? Anything wiiild? I just got in from my niece’s 2nd bday raaaager. Wiiiild times …

And then he asked her out:

Sorry if a bit fwd but just walked in after the drive and like 😳

They ultimately settled on the next night. When Sam called me afterward, she sounded relieved. She’d arrived first to an eerily quiet, empty bar. But then the man—the former woodworker, in fact—showed up and he was cute and fun to talk to. She was a little surprised that he’d gone into such detail about one particular, fairly obscure interest listed on his profile. But I pointed out that ChatGPT as Sam had expressed lots of interest in it.

There wasn’t an easy segue to “That was actually A.I. and my friend on the app,” but once he’d mentioned a second date, Sam knew it was time. And so, while they were still seated there, a few inches from each other, she told him. He seemed stunned. But then, within a few minutes, they were laughing. He texted her later, reinforcing that the date had survived the reveal. When I reached out to the former woodworker, offering to address any concerns, he suggested that it would be difficult to detect A.I. on Tinder because most “conversations are probably on the level of a chatbot.”

Sam sounded even more excited when I talked to her after another date the next night. On Tinder, he had opened by commenting on the poorly rated sushi photo. “Hi Sam. That is a beautiful sashimi platter!” he wrote.

I’d elevated him quickly because of the algorithm’s emphasis on speaking multiple languages, a shared worldview, and humor. After asking him out, I realized we’d barely vetted him. “What’s a good question for finding out if someone is a decent human being?” I asked ChatGPT. Its long-winded answer was, more or less, I don’t know.

ChatGPT selected the date location, a darkly lit bar full of wood and leather, with a candle on each table. It was a good choice, Sam concluded. She was a little concerned that her date was trying to hide something because he was wearing sunglasses in most of his dating photos. But he looked even better without them. They had lots in common. There may have even been chemistry. He asked more questions about the experiment than the previous guy had, but ultimately it made for an interesting conversation. It wasn’t just a decent dating-app date—it was a great date. She said she’d likely go out with both men again.

Does A.I. deserve credit? I’m not sure. It was helpful the way a thesaurus or Google is, offering inspiration for what to write. But I suspect that the two men she went out with as a result agreed to dates despite, and not because of, some of her unconventional turns of phrase. Even so, ChatGPT encouraged an odd strain of forwardness that was helpful in getting the dates set up quickly. As Sam wrote to me from her plane later, you study people’s profiles to write “the perfect slightly flirty and charming quip” because “we think we can determine someone’s personality or charm in those first few texts.” But maybe they aren’t that helpful and you should just go out as quickly as possible.

Ultimately, Sam and I agreed that the act of outsourcing dating to someone who knows you well was also a large part of why this worked. If only there was an app that let your friends more transparently date for you. Alas, Nagaraj, the venture capital investor, is among those who have tried to create this. They never seem to take off.

In Sam’s case, thankfully, the two men were good sports about all this. I’m sure it helped that they were pleased with the outcome. The former woodworker said it was such an energizing date that perhaps the “system worked.” The multilingual sushi-platter lover was similarly positive. He would later write: “I guess I should thank you, Sam or ChatGPT (or all of the above?) for a very cool evening.”

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