Three hit people - two men, one woman, who have never met before are placed on a road trip down the East Coast together. The only thing they have in common is that they have all worked for the same boss - and, as they swap stories, discover that they have all screwed up for this same boss in the past. As they share their stories of errors on the job - seen through visual, stirring flashbacks - they begin to wonder why it was they were put together in the first place and what might be waiting for them at the end of their little road trip.

When Sarah accidentally proposes to her girlfriend in Provincetown, the mixup turns their loving relationship into a minefield of marital exploration.