Lorelai seemed to meet Dwight on a Monday night, just before the auction on Tuesday. He asked if she could water his lawn, as he was leaving for a few days on an urgent last-minute business trip. As Rory was waiting for her with the pizza, Lorelai tried to put him off, saying that Dwight could show her some other time before he left on his trip. Dwight said he was leaving for his business trip at 6 am the next morning, so Lorelai reluctantly accompanied him to be shown how to use the spigot.
Even though Dwight supposedly left for his business trip on the morning of the day of the auction, Lorelai and Rory are not shown watering his lawn until about a week later – even though the business trip was only meant to be a few days. They have had Friday night dinner, and Rory is now wearing her school uniform, so they are past the weekend, and it is another Monday at the absolute earliest.
Somehow they just skipped an entire week of lawn watering and Dwight is still on his short business trip. I know I usually blame Daniel Palladino for these timeline inconsistencies and non-linear plotting, but this episode was written by Justin Tanner, a successful playwright, and a story editor on Gilmore Girls. This is the only episode he ever wrote.
The Annotated Gilmore Girls 