It’s been a year since Olivia Grayham, a child of the hotel business, struck out on her own as an event planner. It’s been a struggle but she’s finally poised for a major career boost thanks to her best friend Alexandra, who is taking her wildly popular YouTube lifestyle series onto the high seas for a Caribbean cruise. Tasked with organizing a multifaceted event for the fans onboard and online, Olivia has plotted the journey down to the last detail and planned for every possible contingency, or so she believes. She’s no sooner onboard than she faces her first curveball: the ship’s longtime cruise director has been reassigned and instead she will be working with his second-in-command, Tony Rieves, who has already begun putting his stamp on the ship’s activities. With no option but to adjust to each unexpected development that comes her way, Olivia realizes that there are some things that simply can’t be planned or anticipated – like falling love.

When aspiring children’s entertainer Jason gets his long-time crush Danny pregnant on their first date, the two choose to make a life together as husband and wife. As the prospect of fatherhood looms, Jason begins to realize the toll it may take on his career and turns his attention toward one last pursuit of his dreams before the baby arrives. Feeling ignored, Danny begins to question whether their fledgling marriage can survive. The two soon find themselves attracted to other people. Jason meets an intern at a local cable station who wants to develop a children’s show utilizing his talents, and Danny meets a pregnancy photographer who goes out of his way to encourage her confidence. As these new friendships begin to hint at the possibility of romance, Jason and Danny must decide whether they will risk the future of their family for the indulgence of a moment’s pleasure.