How did you manage to proc this? The roommate is max friendship and lust atp. Was starting to think nothing would happen and I'm just doin the same boring challenges over and over. Speaking of which is there a guide to procing events?
This is speculation as I haven't looked into the code:
You need the roommate's partner to have certain dominance over you or have done enough dares.
Then, enter your dorm room while the roommate is inside. There is a random chance for the event to trigger, where they are both there and propose a more extreme dare. It may have to be in the evening.
Best way to proc an event is hitting * on your NumPad. For this event go in the room, see your roommate is there -> hit the back arrow in the game interface (top left) -> hit * to refresh your game instance -> enter room hoping for it to trigger, repeat till it does.
At the end you can take them up on the offer to enter a relationship with both of them. Your roommate may hate you at the time, have 0 lust for you. It doesn't matter. You are now in a relationship, so you can go out with them and slowly build everything up.
If you want to only be in a relationship with one of them, you can break up with the other one.