It was a first date, and it was not going well. Even the server ignored the couple so as not to ruin what was otherwise a pretty good shift.

She was pure "Burberry Becky."

He wore creased blue jeans with a red and black checked collared shirt beneath a gray houndstooth wool vest. It was an odd clash of prep school and the great outdoors. He picked the shirt because it was the only clean collared shirt he owned, and the vest was how he'd "dressed up" since 1998. With his large black glasses,...