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My first computer was a ZX81 - in 1982 - which, with my brother, I built from a kit and was astonished when it actually worked. We eventually added the 16k ram pack too: how could anyone possibly use all that?!
First phone. I think it was a Nokia 5110 or similar in 2000.
At the point where you and the AI can see someone straightening their tie in a certain way and you and the AI can exchange a single wordless glance and you both burst out laughing 'cos it was just like that thing that you both saw 6 months ago and found hilarious then - then maybe.
Not before.