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 ever since they were brought together six years ago in a meet-cute straight out of a romantic comedy.

This summer, Ray convinces Kip to join him for an early honeymoon at a famous lux resort in Ray's coastal New England hometown, eschewing the tradition of bachelor parties and hoping to recharge before their end-of-August wedding. 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?