What Do Women Think When Guys Rely on AI to Flirt?

I knew men were using AI tools to create their profiles on dating apps and draft messages to women. Plenty of single women have received texts that were clearly written by ChatGPT or Claude. Indeed, a recent study found that 26 percent of adults are using AI for help with dating. But then I heard about Kent, a late-20-something finance worker in New York. Kent is the apex predator of AI romance. He audio-records his dates (one-party-consent recording is legal in New York State) and runs the transcripts through Claude for feedback.

“Claude will show me which conversation topics work best, who talked more, what did we spend the most energy on, how many positive words were used versus negative, what got me the most interested,” he told me. “I’ve always been a data-driven guy, and I’m curious to know how I can do better.”

Yeah, it’s weird, but at least Kent is using AI to improve himself, right? Are other guys this conscientious? “At least three quarters of my clients are using AI in some shape or form,” says Connell Barrett, a dating coach in New York City. Many of his clients, most of whom are straight men, are asking chatbots what to say to women. One client wanted to flirt with a Starbucks barista. Instead of just—you know—talking to her, he spent 15 minutes asking a chatbot for a good opening line.

According to Barrett, a perfect storm of circumstance has rendered men terrified to approach women. “One is the #MeToo era, where they are scared of being accused of wrongdoing,” he says. “The other is social media. They see women on TikTok saying, ‘This creepy guy bothered me today,’ so they think they can’t approach a woman or they will get called out online. ... A lot of men think ChatGPT is going to be their salvation, even though it’s a robot and ChatGPT is terrible at flirting.”

Nia Del Mar, a 30-year-old in the Bronx, has chatted with guys on Hinge and Raya who she believes are sending AI-written messages because they don’t sound human. She’s even found herself having the exact same conversation with three or four matches at any given time. Now if Nia suspects AI foul play, she unmatches. “When we meet up in person ... are they going to spend the whole time on their phone looking for responses?

“In a lot of cases, it’s just laziness.”

Some of the dating apps are building AI tools into their platforms. Grindr, for instance, offers a new tool that examines chat history and messages, then ranks and suggests matches.

Another AI tool will scan photos and recommend which ones will elicit the most matches.

Tinder has rolled out a system named World ID in which users can verify themselves as a human and then have a badge next to their name proving they aren’t a bot.

Throughout history, men have taken outrageous steps to get laid. Antony went to war to continue sleeping with Cleopatra! Taking the advice of a robot seems relatively light compared with mortal combat. But heed the warning of Cyrano de Bergerac—remade a century later as Roxanne, with Steve Martin and Daryl Hannah—in which a tongue-tied hunk asks another man to write love letters to the woman of his dreams. She falls in love with the writer.

This story originally appeared on Esquire.com.

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