I was still playing with house money on this trip, and I owed my Wynn host, so I camped out at a $500 per hand blackjack table. I was alone and enjoyed chatting with the dealer. The play was choppy, and I didn't stray far from even. I had a couple drinks and looked at my watch after every hand. It surprised me to be this anxious after Kat had texted me the envelope contained $1,000.

The idea to set Kat up to play escort for an hour had hit me out of the blue but seemed brilliant, so my first instinct was to ask my host at the Wynn...