Flirting With a Bot

Let's hear it for the bots! Just kidding. Behold, a cautionary dating tale.

A few weeks ago, I added the dating apps back to my phone, and after just one crazy exchange was immediately reminded why I’d taken them off in the first/second/third place. I took to Threads, a platform I still don’t quite understand how best to use and posted about it. What do you know? It went sort of viral. The adrenalin kicked in and I spent a few days chatting about the incident with friends and strangers alike, not to mention brain-dumping the whole ordeal into an essay, which I’m including below. For those of you who are not paid subscribers, I hope you’ll consider supporting my writing efforts by upgrading to a paid sub. Thank you for reading, and sharing your thoughts in the comments below and/or via Substack Notes.

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I added the apps back to my phone for the gazillionth time the day after I saw Babygirl. Call me a cliché, but even a single and content 46-year-old deserves a cold glass of milk from time to time.

I never could’ve imagined how dicy the endeavor would be right from the start. We are essentially all now living in a simulation, yet somehow I was surprised to find that my first brush back with dating in the States—after nearly a decade of not really dating in France—involved, what appeared to be, a very handsome bot named Louis.

Or was he?

Shortly after matching with Louis’s profile, which if memory serves said very little other than he was a 43-year-old living in Brooklyn Heights, I learned he was from Manchester, divorced, had an 18-year-old daughter who goes to UCLA and worked as a contractor flipping houses. Seemed specific enough, only his stilted responses grew increasingly vague for an English native. It was his photo that tipped me off, though. Or, rather, tipped off a dear friend, also single, who I’ve known for over 20 years.

“Send me a photo!” she replied when I texted her that I matched “with a handsome man — but like almost too handsome?”

I sent her back his mug, showing his chiseled jawline, perfectly coiffed hair, and furrowed brow. “He is hot!” she replied. I sent her a few more, to which she added: “Looks like AI.”

Photo by Alex Knight

Only slightly offended, I honestly hadn’t even considered it. Maybe I’m just middle-aged and out of it — both literally and figuratively, having not dated in general, and in the U.S., for quite some time.

My friend and I continued to text about it, while I also texted with Louis and simultaneously watched the SNL 50th anniversary show. I guess you can say I was curious, but not too invested. Eventually, I told him I was going to bed to which he wrote, “Good night, sweet dreams, hope to receive your good morning greetings.”

Er, OK.

The next morning, at around 10:30, my phone dinged with a fairly acceptable, “Good morning. How did you sleep?” from Louis.

I replied innocuously, but things quickly spiraled. His choppy, seemingly ChatGPT-generated phrases included, “I just cleaned my room at home in the morning and now I have prepared some ingredients for lunch.” And, when I inquired about his so-called favorite place in his neighborhood: “I especially enjoy walking there, especially at dusk, when the sunset is reflected on the skyline, and is very dramatic.”

I continued to engage because, well, was I the one being weird and judgmental? Have I not dated for so long that I’m giving a human shit for sounding off? Or, am I a complete idiot for not realizing this guy is a bot or pretending to be someone he’s not? I was truly torn. Eventually, I decided to ask him: “Sorry, but is this AI?”

At this point in my life—and certainly in this exchange—I have zero fucks left to give.

Screenshots of my chat with "Louis"

He continued to respond, albeit awkwardly, so I asked for a selfie thinking maybe I’d catch him filter-less in his kitchen preparing avocado toast or something. It didn’t help. The snapshot looked like the others: fake. No clear background. No noticeable wrinkles. Like the ones that come in the picture frames at Home Goods. I was too skeptical, shy, and out of practice to send a selfie myself just yet, so perhaps unfairly I pushed for more details about him: Who made his shirt? Where’d he get it? Where is he at this exact moment? Not necessarily things I’d ask a guy while getting to know them; I much prefer, “What show did you recently binge?” and “Where would you hop on a plane to tomorrow?” but here we were. To this, replied:

“This is my home in Brooklyn Heights, which I purchased three years ago. My daughter gave me this dress and I like it very much.”

There he goes again!

“What’s the problem? A daughter can’t give clothes to her father?”

Sure, but does her father wear…dresses? If so—and no disrespect to any fathers who wear dresses—we’re just not aligned. Was it a typo, as he said? Or was he, indeed, George Jetson’s very hot cousin? Honestly, how does one know for sure?

By now I’m engaging for the sake of entertainment, and also because I’m an inquisitive journalist who hasn’t had a lover in a long time. So I suggested we meet in person to get to the bottom of it. I didn’t have plans for later that evening and knew I needed to just rip off the Band-Aid when it came to moving things along, both in this particular instance and when dating in general.

“I prefer that we meet after we get to know each other, otherwise it will be awkward to meet so suddenly. In the process of getting to know each other, I need to know if we have the same values and interests to determine whether we are suitable before meeting and dating because I am a responsible man.”

Are you, though?

And yet, I couldn’t help but agree. I normally prefer to partake in (ideally witty, not formal) exchanges for a bit longer, too. But in this case, I genuinely wasn’t sure who—or what!—I was talking to.

To make matters even more complicated, he started questioning me, saying I was acting strange, which, to be fair, I probably was! Defending my legitimacy felt ridiculous, but it was all such a mindfuck so I took and sent him a very PG-13 selfie.

The selfie I reluctantly took and sent to “Louis.”

Then…silence. Up until then, our correspondence had been constant. Now there seemed to be a 7-minute stalemate between us.

I couldn’t tell who I wanted to prove wrong: me or him. If my instincts were correct, at least I’m human, but my hopes for dating would once again be crushed. And if they weren’t? Fuck, I’m doomed. Have I grown that cynical and immune to connecting?

Unfortunately, because I am a responsible woman, and maybe both a little weary and wary of committing and being rejected, I decided to just call it quits and block him.¹

So, who lost and who won in this 2025 Dating Battle Royale? Both of us, I guess. “Us” being a two-letter concept—like “AI”—that I may not ever match with on the apps. And maybe that’s OK.

1. Five days later, my brother’s GF offered to call the “business account” number I had for “Louis” from her phone. Not only did no one answer but there was an automated response along the lines of, “The number you have reached…”