On one of his dates, single father Jake meets Meg, but the meeting is awkward, and the couple breaks up. Later, Jake, along with his eccentric family and childhood friend Reuben, goes on a sea cruise, where he unexpectedly runs into Meg on board the ship. As Jake tries to figure out how to approach her a second time, Reuben confesses that he fell in love with her at first sight and asks Jake's permission to pursue her. Jake agrees, but soon realizes that he has made a big mistake.