November in tennis means something different than the rest of the year. The tour winds down, and the pros trade their practice courts for something looser—a beach somewhere, maybe a cocktail with an umbrella in it.

We took our own escape to Oahu, where my wife and I celebrated five years together by doing exactly what felt right: hitting on outdoor courts with trade winds blowing through the nets.

I took a few flicks. 14 to be exact. You know how we do it.