Billy Montgomery, a Houston-born New York transplant, aspiring novelist, and soon-to-be young divorcée is headed to Punta Mita for his sister's destination wedding with a severe case of bad luck, a broken heart, and a sunny disposition about it all. As Man of Honor, he's on a mission to make sure this weekend goes off without a hitch while shoving down his own feelings about being stabbed in the back by love.

Michael Evans, a mid-level public relations expert from Queens, can make anyone and anything look squeaky clean from the outside, but can he do it for himself? When he's asked to fly into Ohio to give a tear-jerking speech at his estranged father's funeral, he wonders if he's met his ultimate PR match that may just send him into a spiral of his painful past.

Through a meet-cute gone wrong, a truly unfortunate baggage mix-up, and a run in with TSA, they find themselves stuck on standby in a New York airport for days on end, waiting on a miracle to get them to their respective destinations. While being stranded between overpriced souvenir shops and underwhelming airport cuisine, they find themselves learning more and more about one other, as well as exposing their own personal baggage that they've been carrying for far too long.

Love, loss, grief, forgiveness, and well, the absence of all of the above drive Michael and Billy to emotional depths together. Can these two tackle the ins and outs of these feelings while also dealing with the possibility of their own blossoming romance?