Emmy Vincent can't believe her besties would sign her up for a matchmaking vacation at a resort in Vermont, but she is guilted into going because the trip is non-refundable. What she never expects is being cheated on hours after she meets her "perfect match". Booker Drummond is tired of dating one woman after another and not finding one interested in a relationship, and he takes a chance on a matchmaking vacation in Vermont, thinking he can't do any worse than he has been, and guesses the fates are laughing at him when his "date" for the week cheats on him. When Emmy and Booker realize they're in the same boat, they decide there's no sense in remaining solo at a resort full of couples, and they join in the group activities during their stay, happy to have someone to spend a few days with. Until the vacation comes to an end and Booker realizes he wants more than just a few days with Emmy.