One day, after Christmas is over, the two have a chance encounter when both are returning presents they received. After Sloane tells him about her Aunt Susan who brings a new date for every holiday gathering, which she dubs as a "holidate", Jackson suggests that they be each other's so he can avoid attachment girls and Sloane can avoid pity from her family. Though she initially declines, she decides to take him up on his offer and the two spend New Year's Eve together. They have a fun time, and although they clearly enjoy each other's company, Sloane declines being his Valentine's Day holidate, believing that the two could find genuine dates before then. However when Valentine's Day rolls around, Sloane runs into her ex boyfriend with his new girlfriend while shopping for candy. Because Jackson is walking by and takes notice, he pretends to be her boyfriend and they leave together. Both agree that it is safer to be each other's holidates from that point on to avoid further trouble, and to stay platonic.