The logic in game of this game is so ridiculous at times. Things like making a cocktail for Brenda, I was carrying around those "cold" drinks for almost a week before I finally found when I could give them to her. (She just wasn't ever in the hot tub.)
Right now she got upset about having Janice come over, wouldn't talk to me, so I slept woke up to her asking for medication. On the way to the pharmacy got asked to give the box to Freya, skipped the hour for the store to open instead of going back to Brenda. Gave the box, accidentally headed back into the store and got the "latex with Janice' scene (Thought I got the bugged out all white screen version).
Woke up the next morning, can't even click on Brenda without me saying she is pissed or her telling me she is pissed. "I got your cold medicine, moron, you said you needed it."
That was a week ago. No idea when I will stumble into the right time for her to either not be pissed, or want the cold medicine.
Almost as dumb as the two times I went to a detectives house at 7 am, she dressed up all slutty and then I brought her to a park to met up with some college kids, at 7:00 am.
Edit: Ended up being 10 days, I had the choice of either giving her the gift or the medicine, I chose the gift just to make myself laugh. Got the scene, next day gave the medicine I feel like two different quests lines got crossed up, and ran concurrently. I have never played this game before.