While most of the focus of Lorleai, too, has a complicated relationship with Richard, but theirs is often a bit more straightforward, as Lorelai has a relatively clear-cut rebellious-teen-strict-parent dynamic going on with Emily and Richard (at least in the early seasons on the show).
Rory and her grandfather didn't get a chance to spend time together until Rory was a teenager, and even then, Richard only re-entered her life because Lorelai needed to borrow money to send Rory to school. From the start, that was going to create a complex relationship, very different from that of a granddaughter who grew up with her grandfather. But did it turn out to be a positive relationship in the end?
Toxic: Purely Mercenary (To Start)
It's not entirely clear if Emily and Richard had any at all with Rory and Lorelai before the show (like the occasional card or phone call), but it seems that there was essentially none - and the only reason that this changed was because of the costs of Chilton, and later, Yale. In general, it's not the healthiest thing for a family relationship to be money-driven like this, even if this clearly changed over time.
Perfect: Shared Interests
Rory and Richard had a lot in common, and it became clear as they started to spend time together that they loved a lot of the same things. They would spend hours discussing literature and history, and her grandfather encouraged her love of books and bought her books as gifts. They also managed to bond over golf, surprisingly enough, although neither expected it at first.
Toxic: He Tried To Shape Her
In many ways, this can be forgiven, as he was trying to make sure she had the best life possible, but both Richard and Emily had a tendency to push Rory to fit with the kind of life that they led, and the social circle that they had.
They pushed her to go to Yale, and he even set up a 'surprise' interview for her there, leaving her flustered and angry because she couldn't prepare. He may have had good intentions, but this had the potential to really mess up her future.
Perfect: Always ive
Much as he could sometimes take the wrong approach, Richard was generally extremely ive of Rory. He thought that she was brilliant, intelligent, and kind, and told her as much. When she felt like she needed a break from school, he was there to her and give her somewhere to stay, and tell her that it was fine to take time off - and while this was the most dramatic time, he was also there to her dreams and aspirations on the smaller stuff, too.
Toxic: Came Between Rory and Lorelai
One of the most dramatic storylines in Gilmore Girls was when Rory quit Yale for a while, and moved in with her grandparents. While this was very ive of Rory, it was also problematic, as Lorelai had previously come to her parents, explained that Rory was struggling, and tried to come up with a t way to deal with it. Instead of doing this, Richard (and Emily) chose to go entirely against Lorelai's wishes, and not communicate with her to work something else out, either. This drove a wedge between them, and plenty of fans wondered if this was a little intentional, too.
Perfect: Had Fun Together
One of the sweetest things about their relationship was that Rory and Richard clearly had fun! When Logan was bugging Rory with his attentions, interrupting her class at Yale, she got her grandfather to essentially prank him, pretending that he was thrilled and expecting a proposal any second.
It's not the only time the two were joking around together, either, but it's the one that really stands out.
Toxic: He Often Ignored Her
ittedly, this is just a toxic trait of Richard's, as he had a habit of ignoring everyone in his life from time to time. There were times that Richard got so caught up with work or his own stresses that he would be late to the weekly dinners he had with Rory, would barely speak with them while there, would be away on business, or would even be barely paying attention (like at her debutante ball). It was hardly a great part of their relationship.
Perfect: Clearly Devoted
For all his faults, there can be no doubt that Richard absolutely adored his granddaughter, and he always made that clear. He complimented her, and defended her on the rare occasions that someone else would put her down. He was willing to be there for her, was always there to answer her call, and would have done or given her anything - money or otherwise.
Toxic: Looked Down On Her Life
This is another issue that can be forgiven somewhat because his intentions were good - and Richard only ever wanted the best for Rory, and for Lorelai. However, he (and Emily) often seemed to look down on the lives that they led in Stars Hollow, whether that was his surprise at Rory's suggestion of a frozen pizza one night, or comments on their clothing, finances, or eating habits in general. He didn't mean to be patronizing, but it often crossed the line from concern to insult.
Perfect: Became Truly Loving
In the end, this relationship was far more loving than toxic, and was able to grow and develop into a real friendship as well as a loving familial relationship. When Richard ed away, Rory was heartbroken, and it was clear that she really valued her grandfather for himself, and for how close they had become. This may have started because of money, but that soon became only a tiny part of what held these two together.