My immediate thought was Harry Harlow's wire mother/rag mother experiments with Rhesus Monkeys (CW: live animal experimentation - https://en.wikipedia.org/wiki/Harry_Harlow#Monkey_studies) which were an early exerpiment showing that it's really, really bad for primates to be socially isolated. A bunch of polar expeditions were demonstrating the same thing about a decade prior.
Recently we've had a whole bunch of movies about men failing the Turing Test regarding their digital waifus - Blade Runner, Her, Ex Machina, Archer. There are like five different TvTropes pages directly related to this question. And you can go back all the way to Hellenic Greece, with the story of Pygmalia and Galatea, to get the OG "Incel falls in love with body pillow" narrative.
The most consistent AIs to get the Loebner prize were the ones who could talk about one topic and stay on it. Seems like humans interpret things such as sudden conversation breaks as jarring, like a sudden change in the topic or the AI forgetting something that was said earlier.
As in, seems like the easiest way to make an AI seem human is to make the human more emotionally invested in a single thread of conversation, because then the human will fill in the gaps with their own perception. We'll imbue the AI with ourselves. It's like Tom Hanks talking to the volleyball.