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Just wanted to update this and say as of 0.3.27 these bugs are still present even on a new save. After starting a new save, I noticed the game doesn't assume you sleep with Cait until day 7. So even if you just sleep from day 1 to day 7 the dialogue will randomly change to imply you've hooked up.

When I talk to him about Cait my character says they've fucked her even though they haven't. I went back to an earlier save and had the same problem. The second part of his sleep with scenes/the waking up part no longer trigger when sleeping at a campsite. In his holiday event's present sex...