She drinks too much coffee
She doesn’t eat grapefruit with breakfast (she has a banana instead)
She doesn’t wear sensible shoes to work
She doesn’t dress appropriately for work (how does Lorelai not have a jacket? It’s winter!)
She didn’t have any tablecloths in the dining room due to an issue with her linen delivery
She spoke flirtatiously to her linen delivery guy in order to get better service
She got out of the car before it had completely come to a stop
She ordered Chinese food that wasn’t authentically Chinese
She buys more food for dinner than she can eat in one sitting (they eat leftovers)
She pushed Rory into wanting to go to Harvard without even investigating Yale
She allowed Rory’s seventeen-year-old boyfriend to rebuild her an old car
A few of Richard’s criticisms are reasonable. The ones about Rory are instigated by genuine concern for his granddaughter, and wanting her to be safe. Many of them are based on an old-fashioned view of the workplace, and a complete lack of understanding of the hospitality industry and female management styles. Some of his criticisms are ridiculous and extremely petty.
None of them are appropriate for him to share with Lorelai on a day that he is coming to visit her home and workplace as her guest. She is a woman in her thirties with a teenage daughter, her own home and car, and a good job. No matter what Richard’s opinions are, he shouldn’t berate Lorelai for her lifestyle choices, and especially not in front of her colleague, Michel.
The show focuses especially on Lorelai’s fraught relationship with Emily, but Richard and Lorelai certainly have their issues.