Idk if this is a glitch but.... every time I hang out it Guillermero's room the hint says I need to hang out in his room and idk what the game sees as evening...
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How far into the game are you? Have you had a “Talk About Sex” conversation with the Best Friend(thats the technical term for what Guillermero is)?
My next paragraph is somewhat spoiler heavy for how you start the process of growing closer with The Best Friend, but not that bad for the two ways you get in really deep.
If your doing what I think you are its actually simple, go to the Main Hall at any time between 6:00 PM and 10:59 PM, I strongly recommend going to their room every night, there are some chance based things you need to not happen and you need to have 2 specific events happen within the “Talk About Sex”
It sounds like you've just started this game. Then you should go to hints. And see where in the BF storyline you are. My suggestion go to the Friday Parties. Try to build up your Party Popularity, or Start Sucking dick and Drinking the Milkshakes. Oh yeah don't forget to swallow like a good girl. Eventually you'll be prompted to investigate how the milkshake are made. Do it tell your BF. Afterwords you'll be able to go back to their room to talk about sex.