Richard Gilmore is a prominent businessman in Hartford. He works in the insurance business. His business situation changes during the series. When the series begins, he works in a company owned by Floyd Stiles. After a brief forced retirement in S2, he opens his own international insurance consulting business. Richard is completely helpless in setting up his new business without his secretary, so his daughter has to show him all the marvels of the office supply store, as well as find him a new Margie - Margie being his secretary at his old job. Karen, his new assistant, does a perfect job of supporting his new business venture. Richard takes on a partner in S4, Jason Stiles, his former boss's son. After a messy legal situation, Richard rejoins Floyd's company as his own separate business. In S7 he teaches an economics class at Yale.Richard is graduate of Yale and was a member of the Wiffenpoofs while there. He is married to Emily Gilmore, who keeps track of his social schedule and sees to it that all his clothes are in place for his various social and society engagements. He is one of the traditional gentlemen who expects to bring home the paycheck while the women in his life (his wife, his secretary) cater to his needs, the ones that he as a man would not take care of for himself.Richard is very close to his mother, the first Lorelai Gilmore, whom he refers to as Trix. He helps her to move to Hartford late in her life and is all but oblivious to the constant criticism that Trix inflicts on Emily. Richard often refers to his mother as a saint, even though anyone can see she is definitely not one. He is deeply saddened when his mother dies, and he is unable to lift a finger to prepare for her funeral or any of the other last arrangements.Richard has a rocky relationship with his daughter, Lorelai. He wanted her to marry Christopher when she was pregnant and have Christopher work at the company with Richard, but Lorelai would have none of it. He always wants his daughter to do what is expected of her, but she rebels against these types of demands. So though he obviously loves his daughter, they are never very close.When Lorelai comes to her parents for money for her daughter's education at Chilton, Richard is ready to write the check; it's Emily who insists on the Friday night dinners. However, when Rory needs to learn a sport, Emily talks Richard into talking Rory to the club for golf. Much to Richard's surprise, during the golf outing, he and his granddaughter find they are much alike and share a love of reading. From this time onward, they compare with each other the books they are reading. He even picks out rare books for Rory when he travels or has other occasions to give his granddaughter a gift. When he is not giving her books, he gives her money for travel, another love they both share. The type of closeness he never had with his daughter he is pleasantly surprised to be able to share with his granddaughter.Richard works hard and plays hard, but doesn't take the best care of his health. He's in the hospital with heart trouble twice during the series, but doesn't like to make the changes to his diet and lifestyle that are required to keep him healthy. This could make it difficult for him to keep his promise to Emily that she can go first. Even so, he tries his best to meet his obligations to his family, as he sees them to be. Show less «