It was a stunning fall day in New York City, and Jess and I had just finished a beautiful morning at MoMA. We walked into the adjacent restaurant, the Modern, to eat a late lunch at the Bar Room. We drank red wine as a buffer against the slight chill in the air outside. Fewer things gave me more energy than enjoying New York in perfect weather, and I wanted to enjoy that this afternoon.

"I'm done with museums today," I said. "Let's do a wine crawl. I want to show you my favorite spots and just get drunk."

"That sounds amazing," Jess said. She rested her chin on her...