Yea its one of those long questlines. Kinda like the classroom bully. You have to wait till their partner starts challenging you to Dares. While doing the dares one random day. You'll come to your room to find them... Taking care of themselves. As their partner has been more focused on you than them. After witnessing this you then have to go talk to the partner. Where they will set it up for you to fuck your roommate. Unfortunately that's all I know as I accidentally cut it off. Back during the frat house update. Because of the one week deadline, and I immediately moved in to the frat dorm. Literally the next day after I got accepted. And I've been restarting every new release. As updating the game fucks up my porn career. Because all of my recordings just end up becoming. sadistic, took cumshot, humiliation, took facial, pissed on someone, took cumshot, gave facial or creampie. Hope this was somewhat helpful.
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.