Wippa's been diving into a fun new feature of A.I. that lets you have real conversations with it. Unfortunately, he discovered it right after hearing about a guy who fell in love with his A.I.—cue an awkward interview that even included the man's wife... Meanwhile, the Singles Party is heating up as we keep adding names to the guest list and we find out who on the team is the ultimate flirt? Plus, we’ve got wild charity challenges, sports fans losing it on talkback radio, and updates from the rising tensions in Iran.