Sloane is a young woman living in Chicago, Illinois who hates the holidays due to the judgement she receives from her family for not being in a relationship. Having recently broken up with her boyfriend, her mother Elaine is constantly trying to set her up with a new man, much to Sloane’s annoyance. Meanwhile in Evanston, Illinois, Jackson is a young Australian golfer stuck spending the holidays with a girl he has no interest in pursuing a serious relationship with and her family. Later in the night, his date becomes angry with him for not getting her a Christmas present, and he leaves in frustration.
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.
After spending Saint Patrick’s Day and Easter together, it is clear that the two are becoming genuine friends. However, by the time Cinco de Mayo rolls around, they end up getting drunk and the next day, it is highly implied that the two had sex the night before. While Jackson doesn’t seems to care whether or not they did, Sloane vehemently denies it and they go about their lives – pretending nothing happened.
By the Fourth of July, Jackson has become quite close with Sloane’s family and is good friends with her brother York. While setting off firecrackers, Jackson blows his finger off and Sloane is forced to drive him to the hospital to have it reattached. The two get high at the hospital and run into Farooq, a doctor Sloane’s mother tried to set her up with; she flirts with him and Jackson becomes visibly jealous. They go back to his place where they end up touching hands and experience a moment of attraction to one another. Jackson becomes fearful that he and Sloane will become too serious and decides to find a new holidate at the suggestion of his friend Neil. While she brings Farooq as her date to her brother’s wedding to his girlfriend Liz, he attends the wedding with her aunt Susan. However, their dates end up becoming attracted to one another while at the wedding, and the two decide to resume being holidates for Halloween. While at a costume party together, Sloane’s sister Abby becomes acquainted with Neil and the two hit it off even though she is married. Sloane and Jackson also run into her ex boyfriend and his girlfriend again, and it is revealed that she is pregnant. Sloane becomes very upset and is given a drink with antacids by her sister, which makes her sick and forces her to leave. Jackson takes her back to her place and takes care of her until they end up falling asleep and having sex the morning after. Sloane is clearly embarrassed by the whole thing and makes Jackson leave, believing that they made a mistake. Later, Abby comes by the apartment to tell her that she ended up kissing Neil, which Sloane promises to keep a secret.
When Thanksgiving comes, Susan has arrived with another holidate named Walley instead of Farooq, much to everyone’s disappointment. Later Jackson shows up and he and Sloane go to Sprouts to get items for dinner. While there, he tries to talk about what happened but she does not want to discuss it. She reminds him that when they first met, he told her that he wasn’t attracted to her, and believes that he still isn’t. He tells her that he lied when he said this in order to get her to say yes to his holidate offer, but she still refuses to accept his apology. Later in the day, Wally ends up having a heart attack and aunt Susan takes him to the hospital with Sloane and runs into Farooq again. After Sloane encourages her to try to achieve real love again, Susan confesses to Farooq that she has feelings for him, and the two kiss and become a couple.
In the days leading to Christmas, Sloane follows Jackson but is still reluctant to speak to him. When shopping at the mall with her sisters and niece, they notice him walking by and the girls encourage Sloane to go after him. The mall choir helps her out in getting his attention and hands her a microphone. In front of hundreds of people, she confesses her love for Jackson and the two embrace and begin dating. The end credits reveal that all of the couples are still together, and Neil ends up dating Jackson’s date from the beginning of the film.