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Man, all games are broken when the first people who aren't developing them play them. Such is the nature of game development.

Oddly, the romance one is the only quest I was really sure it happened on. There was something else, and I can't remember what, so it was on my mind, and then it happened with that one and I went 'okay, no, that's real'. But, if you can't trip it, I must've done something weird. I'll see if I can repeat it, next time I play.

Okay, it took me a while before I could sit down and playtest properly, but I finally found the bug with the romance sidequest (it only triggered when the faction score was in a specific range); the boxes for Steve's chair quest are more obviously marked, & I confirmed that it's not that quest that's blocking sleep (hint: Joey wanted to do something before you head to bed on day 7, check your quest log!)