Richard knew the second she walked in that she needed money. It wasn't a holiday, why else would she be here? He was happy that Rory had gotten into Chilton, but he barely knew the girl. Lorelai had made sure of that. He heard Emily come up with a condition for Lorelai; that they had to come to dinner once a week. He knew that Lorelai's visit meant so much to Emily, which is why he wrote the check. She would do anything to get to spend more time with Lorelai. Her visit, however, brought back the pain. Over the years, the pain had diminished. He knew that once Emily and Lorelai got into their first argument, it would be back.
Richard was right. Lorelai had taken offense to something, and it had resulted in an argument. He had gotten a quick chance to talk to Rory, and she seemed to be a very intelligent young lady.
Emily had wanted him to get to know Rory, so they went golfing together. She was a terrible golfer, but they had had excellent conversation.
As the Friday nights rolled on by, he found himself enamored of this girl. She was the perfect granddaughter.
He didn't dread the Friday nights anymore. Yes, there was still conflict between Emily and Lorelai. But he had Rory. It was the perfect introduction to what could be family. It was a change from the pain that occured every time Lorelai was mentioned.