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do you know how long it takes for the PC to walk in on the roommate? I've been doing the dares for soooooooooo long, I'm starting to think my game is bugged and i should start from scratch lol

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Eh allegedly it's more easy to trigger on the weekends. So I'd say if they're in the room on Saturday during the day/evening, and you've maxed out  their partner. Then save it and just keep going in and out of the room. Soft reset till it prompts I've seen some people say that works. I've never really tried this method intentionally. And the time I did advance the roommate story. I had just finished walking around campus in a towel with their partners cum on my face. For what had to have been the 100th time. When I accidentally prompted it. I was actually trying to get stuck in the washer machine. So I was running back and forth doing laundry, exercising in the room to pass tome, and taking showers when my bar dropped down to gold. When around 6 I know this because I could go to my bestie's room. I caught my roomie practicing in some self love. However that was on a Thursday for me. Because the very next day at the quad party. The Greek house leader came and started Rush week. Which I heavy focused because new continent. And once that was over like I said I immediately got the new room. Which back then just broke the quest.