"Break the wheel" sets Gillian's flag to false and makes Ian automatically reject her invite. So i don't think it can be used to determine anything beyond "engage with Gillian at all", especially since breaking the wheel is only possible if Ian has active romantic relationship with another girl.The scenario I am proposing can be coded as such: Ian views the dream (v11_gillian_dream = 2) and Ian does not "break the wheel" during the second dream. Then when the meeting happens there will probably be another choice to lock Ian into that route.
So, since leaving the wheel intact is basically mandatory if one wants Gillian content, that would make the cuck aspect hinge entirely on that single dream choice and like i said, i'd hope the player would have ultimately more control over the outcome than that.
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