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.
100%, if you want to see female focused lonely / kind of sad nsfw or romantic chatbots designed by or aimed at women check out chai.ml, it's essentially character.ai without the nsfw filter, and as such most chatbots are like nsfw fan fiction.