Ray Bruno and his fiancé Kip Hayes are horrible on paper. Ray is a chaotic millennial writer who's been oversharing his every thought on the internet since he was a teenager; Kip is a pragmatic Gen X medical doctor who values stability and privacy in his personal life above all else. But somehow it works. The pair has been madly in love for 6 years. This summer, Ray convinces Kip to join him for an early honeymoon at a famous lux resort in Ray's coastal New England hometown. But when a surprising encounter with another couple at the resort leads to a series of mishaps and miscommunications, Ray and Kip are forced to look at their many differences in a stark new light—thereby turning the trip into less of a vacation and more of a test: will they be able to work through their issues in time for the big day? Or is this marriage over before it begins?