When Katie first arrives on the base, Jerry runs to the plane to help her down. He can be heard saying, "I didn't expect to see you this year!" Katie replies, "Yeah, well I guess you got lucky." This implies that he didn't expect to see her.
However, later on that night in Katie's room... Jerry brings her a bowl of ice cream stating that it's strawberry (her favorite). She replies by reminding him that strawberry is his favorite flavor, and he says.. "Yeah, well you got here early. I didn't have time to go shopping." This implies in a playful way that he DID expect her, and that she showed up early.
Now, I assume it's just him being sarcastic. He obviously can't go shopping in the Arctic. It could be just the way that Paul Walker delivers the line of dialogue that throws me off. However, was Jerry expecting Katie to show up?