Plot Synopsis

Every Christmas, professional Secret Santa Tom helps clients give their loved ones the perfect presents. Though he typically avoids working for people he knows, when his former fraternity brother Paul asks him to find the perfect Christmas present for his girlfriend Jenny, he reluctantly agrees. Through a personality profile that Paul fills out, and through good, old-fashioned surveillance, Tom learns more about Jenny, who recently moved to Chicago with Paul after he was offered a big job. At Paul's behest, Tom joins Paul and Jenny for dinner to learn more about her. At dinner, Jenny recruits Tom to help her plan a holiday event for her non-profit. The more time Tom spends with Jenny planning the event, the more he grows fond of her. Though a spark begins to grow between the two, they are both too loyal to Paul to act on it. As more time passes, Jenny starts to suspect she and Paul are not on the same page about their life goals. One evening, Tom joins Jenny for some pizza when Paul has yet another late night at work. Swept up in the fun of the evening, Tom and Jenny kiss. Jenny immediately feels guilty, and pulls away. When Tom confesses what happened to Paul, Paul socks in the face. Though Tom is no longer helping him find the perfect present, Paul refuses to give up and proposes to Jenny. Jenny rejects his engagement, and they break up. Before Jenny is able to tell Tom, though, she finds out that Paul had hired Tom to research Jenny and find her a perfect gift. Jenny feels betrayed, and tells Tom she wants nothing to do with him. Both rejected by Jenny, Paul and Tom make up and connect over their mutual misery. Paul realizes he was never meant to be with Jenny, and encourages Tom to try and win her back. For a woman as special as Jenny, Tom will need to pull out all the stops to make her holiday wishes come true -- and to make his wish of having Jenny in his life come true as well.