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I handed over my dating life to AI. I don’t think she’ll see me again

TL;DR

Columnist Rhik Samadder handed his dating communication over to AI in week five of his AI diary experiment – with deflating results.

Key Points

  • The AI-generated responses were technically coherent but emotionally hollow, producing what he describes as an 'uncanny valley' conversational style.
  • The outcome: his date likely won't agree to a second meeting, making this a real social casualty of a tech experiment.
  • Samadder, a self-described AI skeptic, questions whether AI can substitute emotional authenticity or whether it actively undermines it.

Nauti's Take

You don't have to be an AI pessimist to recognise that 'let AI do the dating' is a fundamentally broken idea. Dating works through resonance – two people reading each other in real time.

An AI delivering optimised responses disrupts exactly that process. The result isn't a better first date; it's algorithmic catfishing.

That the experiment failed is no surprise – what would have been surprising is if it had worked.

Context

Dating apps are already experimenting with AI assistants that suggest messages or respond autonomously. Samadder's experience illustrates what gets lost in the process: the unpolished, genuine self that makes a person compelling. When AI takes over the first impression, it creates a facade – and the other person is essentially going on a date with an algorithm.

The deeper question is serious: who bears responsibility when AI-generated words spark or wound real emotions?

Sources