AI
How startup founders are using AI agents to automate dating—from mass DMs to breakup scripts
Entrepreneurs are leveraging OpenClaw and other AI tools to streamline dating, from bulk messaging to venue research, raising questions about authenticity and where humans should draw the line.
TechCrunch — AI
Entrepreneurs and tech workers are increasingly turning to AI agents to automate aspects of their dating lives, from orchestrating mass outreach campaigns to composing personalized breakup messages. The trend highlights both the creative problem-solving potential of AI tools and the ethical tensions that emerge when automation enters intimate spaces.
Shooting for scale: the mass-messaging approach#
Content creator and startup founder Ben Guez has devised an elaborate system to attract romantic interest using OpenClaw and Claude. He uses the AI agent to monitor World Cup results, then automatically triggers Claude to generate and publish nearly identical Instagram "trial reels"—videos that don't appear on his public profile but reach viewers through feeds.
The videos follow a formulaic template: Guez gazes pensively out a train window with a caption tailored to whichever nation just lost: "I can't believe {COUNTRY} lost… If any {COUNTRY} girls need emotional support… my DMs are open." He has deployed this script over a dozen times with different country names, amassing more than one million views and 200 direct messages in just a few days. The women who respond must download his language-learning app, Canary, to message him.
When asked if recipients felt deceived once they realized his interest wasn't genuine, Guez noted that women he spoke to actually seemed impressed. He framed transparency about his methods as justification: "I think as long as you're open [about] what you're doing, I think it's fine." However, TechCrunch was unable to independently verify those reactions.
The softer touch: research and logistics#
Other technologists are using AI agents for less controversial dating tasks. Jeff Weisbein, a tech PR founder, employs OpenClaw to research restaurants and entertainment venues across South Florida neighborhoods he's less familiar with. Rather than manually searching, his bot compiles recommendations with links and rationales tailored to the type of date. He does not hide his use of AI from dates, though he acknowledged one woman's negative reaction: "I hate AI agents."
Weisbein draws a firm boundary, however. He refuses to use AI to automate direct conversation with dates or to optimize swiping behavior, calling that approach unsustainable. The distinction he makes—between using AI for logistics versus human interaction—reflects a broader discomfort with delegating the interpersonal core of dating to machines.
