At the wedding, Lorelai lets her parents know that she and Christopher are back together – even though Christopher still hasn’t broken up with his girlfriend, Sherry! A teensy detail that nobody even bothers asking about or suggests might need a little more thought (or at least waiting for Sherry to get back from her business trip).
While Emily and Richard are quietly pleased about the news, Rory is by no means automatically thrilled about getting Daddy Dearest back in her life. In fact, she is justifiably suspicious of his motives, saying that both she and Lorelai have been waiting for this for a long time, and they cannot take another disappointment from the ever-disappointing Christopher.
Amusingly, she warns Christopher, “We take disappointment extremely hard. I mean it. Property damage is often involved”. In the next season, Rory and Lorelai will resort to property damage due to their romantic disappointments. It’s also a foreshadowing of Rory’s even more spectacular disappointment and property issues later on in the story.