Goofs

When Jake is running from the van, the guard rail beside him seems to end, but in the next shot it appears to be continuous and unbroken.

When Nolan is talking with Jake in the van while driving, he holds a tomato in one hand and a hamburger in the other, but when he hands them to Jake (to catch Allie and Eddie), he only hands over the burger; the tomato is nowhere to be seen.

In the very first scene, Ian is locked in a wall locker and passes Jake his mail, math test, and Dave Matthews tickets downward through the locker's lowest vent from the inside. When the locker door opens we can see that the lowest vent is level with the shelf. There is no way Ian could have reached above the shelf to pass the objects down through the vent.

Jake's watch switches arms a few times in the opening scene in Allie's bedroom.

When Jake and Nolan are driving in the van Nolan is eating the burger with the loose tomato that he dropped before he hit Jake. But Jake comments that Nolan has been saying the same thing for hours. That is a long lasting burger.

The college is depicted as having lockers like a high school. Colleges do not have lockers.

Jake travels by hitchhiking across the country to get home in time for Christmas. When he first realizes he's stranded in the desert and finds a phone, why didn't he call a friend from school for a ride back to school? Or a cab? Or even hitchhike? Once he got back to school he could not only call and leave a message for Allie, he could get his ticket and fly back home.

There's no reason for Eddie to drive through Wisconsin where the Santa run happens when traveling from California to Larchmont, NY.

After Jake wins the Santa race, he goes to a local bank to cash his check. He would not have been able to cash the check without an ID.