I had the same problem. In the end, I restarted the entire playthrough because I could no longer continue. The part that I apparently missed or skipped somehow was “In the evening, she’s usually talking on the phone in her room.” It seems the events have a specific order: first, you need to go to her room at 7:00 PM, and then trigger the living room scene at 9:00 PM.My only hint is on the main character "I have a feeling i should focus more on olivia"
After that, I finally received the second blackmail message.
I’m using cheats, so I don’t think that’s part of the problem.