Kristin Cavallari, a writer, has inhabited many places throughout her lifetime. The driver’s seat of a Range Rover, an infinity pool, at least one college classroom—all kinds of places. But where is she right now?

Rich: I thought we were going to use the actual spa and I wondered what it would be like to be topless around you, Caity. Would it change things? Would it bring us closer or push us away from each other? I guess we'll have to figure that out on another day, when we go to water slides.