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Talk to amy and ask whats up with Derek
Talk to Stephanie and ask about his cat
Move the cat picture in the speakers room to reveal a voice recorder
Listen to the voice recorder
Not 100% cos I'm just going by memory and that doesn't really seem relevant to the new conversation that it unlocks, but I'm pretty sure that's what did it. Pretty sure after doing that you will have access to more conversation options which can lead to this achievment, just need to admit you're not really into art.
Not a bad idea to save after getting the recorder but before speaking to Derek, because there are like 3 different paths that branch out from this point.
The second option is to talk to Amy or Frank about Derek, then talk to Steph and after that move the cat picture that's close to the blue sofa. Listen to the voice recorder, then loop it and use it with the window in the art room.