Devolution
Member
Disengage. After his reiteration of his desire at the 10:16pm comment she could have dropped out of the conversation. He said he was put up for this with a challenge, he's still being weird with her. At that point just stop indulging him.
Or let him keep going to make the world understand a typical day at the office when you've had enough. People want this stuff aired. There you go.