Few writers are as dexterous across mediums or as prolific as Cindy Chupack. Her ability to be as heartfelt as she is hilarious is evident in her essays in The New York Times Modern Love section, storytelling at The Moth, and episodes of Sex and the City and Modern Family. Her writing is prescient without being proscriptive, earnest without being cloying, and she can make me laugh and cry sometimes in the same paragraph.

In our interview, Chupack spoke about her most recent book THE LONGEST DATE: LIFE AS A WIFE, which delves into the arbitrary yet real challenges of giving birth, parenthood, and marrying a cool drink of water. (Now you'll know why I turned down Ryan Gosling). A consummate writer, Chupack adapted the book for television and director Jake Kasdan is already shooting the pilot for FOX.

If...