Plot
In December 2001, Ethan loses his parents in a car accident. His best friends Isaac and Chris resolve to spend every Christmas Eve with him so that he will not be alone.
The trio continue their holiday tradition every year until 2015, when they finally decide to end it, as Chris has become a famous football player while Isaac is married with a baby on the way. Both worry that Ethan, a struggling musician working dead-end jobs, is not ready for the tradition to end.
At work, Ethan finds and steals tickets to the exclusive Nutcracker Ball party within New York City. Before embarking on their last Christmas Eve together, Isaac's pregnant wife Betsy gives him recreational drugs, including magic mushrooms and cocaine.
To please his teammates, Chris purchases marijuana from their former high school dealer Mr. Green. At the karaoke bar, the trio runs into Diana, who broke up with Ethan three months ago due to his failure to commit and refusal to meet her parents, and her friend Sarah, both of whom are also attending the Nutcracker Ball. Isaac, affected by the drugs, records a video message confessing that he is terrified of having a child. Chris hooks up with a supposed fan who steals his marijuana.
The friends contact Mr. Green for more marijuana. Isaac realizes he accidentally switched phones with Sarah when he begins to receive sexts. The thief steals Chris' marijuana again, and the friends split up, as Chris wants his marijuana back and Isaac wants his phone, leaving an upset Ethan behind. Chris fails to recover the marijuana; Isaac, hallucinating from drugs, runs into Betsy and her family at church and vomits on the church floor during Midnight Mass. Ethan is beaten by two drunk pub crawling men dressed as Santa Claus after a confrontation.
Meeting back at the subway station, the tension between the friends explodes as Ethan reveals that they know Chris' sudden success is due to steroids, and Chris reveals that he and Isaac think Ethan is lost and not doing anything with his life. Nevertheless, the friends go to the Nutcracker Ball. Chris learns that his teammates did not need the marijuana he struggled to obtain, and mock him. Ethan meets Miley Cyrus, under whose encouragement he spontaneously proposes to Diana in front of the entire party. While she accepts publicly, Diana angrily declines in private, saying that he only proposed out of fear of being alone.
Ashamed and hurt, Ethan goes to the roof where he finds Mr. Green, who reveals that he is the creator of the Nutcracker Ball. Ethan believes his friends no longer need him but Mr. Green makes him experience the memory of his friends creating their yearly ritual that first Christmas after Ethan lost his parents. Ethan then finds Chris and Isaac calling for him after being thrown out due to an altercation with Chris' teammates.
As morning dawns, the friends reconcile. Mr. Green is revealed to be an angel, helping the friends in order to earn his wings. At the hospital after a false labor alarm, Isaac shows his wife the video; she finds it funny and admits she is also scared about becoming a parent.
The trio spend Christmas at Isaac's. Chris admits to his steroid use to his mother. Ethan goes to Diana's, where he apologizes for his commitment anxiety. Diana accepts his request to finally meet her parents.
One year later, the trio and their loved ones spend Christmas together. Isaac's baby cannot sleep, so the friends serenade her.
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