Cory and Shawn both get jobs so they can by Christmas presents for their family and friends. Cory is working at a restaurant called Paulie's and Shawn gets a job down at the docks.
Cory's job turns out to be better than he imagined. The restaurant is pretty much empty, but two men in the back, Mr. Fontaine and Mr. Martini, tip him generously for running various errands. Shawn isn't so lucky. His job starts at 3:00am, the docks are freezing and the work is hard labor.
Cory brings Shawn to work to show him his cushy job. The men give Cory an envelope to deliver to a previously non-existent mail box. Shawn sees what's going on and informs Cory that he's working for the mob; and not the nice mob. Cory has reservations about this and quits. Shawn hangs back to tell the men that Cory is a good guy and wouldn't say anything. Impressed by his loyalty, the two men offer him the now vacant position.
Cory wants Shawn to quit, but Shawn assures him that it's just a job so he can afford Christmas presents. However, when Shawn buys Cory a watch and Cory asks him again to quit, Shawn says he can't give up easy money. He promises Cory that he'll spend Christmas eve with him, like he always does.
On Christmas Eve, Mr. Martini and Mr. Fontaine give Shawn 200 dollars to exchange a box for an envelope. While waiting with the box in front of a warehouse, Cory finds him, saying he shouldn't be doing this for two people that don't care if he lives or dies. Shawn says that getting money for gifts for friends make him feel important; and maybe this is where he belongs. They discuss the situation, with Shawn eventually expressing regret. Remembering The Road Not Taken, a poem read in Mr. Turners the boys agree that the difference between the poem and their situation is that Shawn doesn't have to choose his road alone--he has a best friend.
Meanwhile, Eric says he'll drive Lonnie 500 miles to visit her family in the mountains. However, they get trapped in a blizzard. Eric panics, bangs his head against the window and passes out. The two eventually find their way back to the Matthews' house, with Eric delirious. Lonnie tells the tale, and then admits to Eric in private that it was more serious than she told. She says that she even had to keep them warm, by stripping them both naked and cuddling in a sleeping bag. Eric, of course, is really upset because this happened while he was unconscious.