Jake (Mulroney), a single dad, sets off on a cruise with his quirky family and childhood friend, Reuben (Green). Onboard, he unexpectedly crosses paths with Meg (Akerman), a woman with whom he once had an awkward and unfortunate date on the mainland. Smitten with Meg, Reuben asks Jake’s permission to ask her out, which Jake grants. Soon after, Jake begins to develop feelings for Meg and realizes he made a mistake by allowing his friend to pursue her. Throughout the cruise, the pair battle it out, each trying to one-up the other in hopes of winning her affection.