When you start to 'play with him' there is a greyed out option thats the new event
Are you refering "him" to the character that is standing outside the room where there are three people inside? If yes, i do notice the greyed out button when i played it a long time ago. But now, i can't repeat it because i've finished the event.
Note: right now, i make a new character so if you're refering "him" to what i said earlier, please tell me how to trigger that greyed out text again. Because the last time i played i just got lucky and didn't know what he want