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Winter needs a friend he can share things with so that he's less in his head all the time, someone cool and understanding with whom he can air out these sort of situations. Not a psychiatrist and not his crush. Just a good friend. Whether he is "right" to have these expectations or not they are to be expected because a part of him knows Gyeo-wol is interested. Gyeo-wol gets super involved in his life and then draws a neat line in the sand, on the grounds of being frank about work priorities. Of course, seeing dating rumors right after would make Winter feel confused and lied to not just as a crush turned down but as a *friend* who expected honesty but sees behaviour that seems to state otherwise.

That's what the therapist means when he says Gyeo-wol can't treat ppl like cats. You can't rely only on practical gestures when emotional matters need to be addressed. And he knew lol. He knew how Winter would feel, Gyeo-wol is thinking about Winter too in this moment, but he avoided communicating with him about it because, among other things, it would acknowledge their emotional bond despite everything.