- ‶One wrong man can always find a friend″
Richard was married to Emily Gilmore and is the father of Lorelai Gilmore and the grandfather of Rory Gilmore. His mother, Lorelai "Trix" Gilmore, also appears in several episodes. Richard is a stern, hard-working, old-fashioned husband and father, who enjoys cigars, golfing and brandy. He rigorously adheres to the traditional life of high society, with its class structures, rules and concepts of appropriate behaviour.
He does not tolerate any form of scandal, but shows glimpses of perhaps not a really emotional attachment to the trappings of his and his wife Emily's lifestyle. While at moments throughout the show, it's obvious Richard has deep affection and admiration for his daughter, Lorelai, he adheres to the confines of his societal standing, and Emily's broken heart, and does not easily forgive Lorelai for leaving the family as a teenager.
At the start of the series, Richard is the Executive Vice President of the Gehrman-Driscoll Insurance Corporation, and he oversees their international division. He has taken on several different ventures since he was initially forced into retirement. He gets a teaching job at the Yale University where he holds lectures on economics, which are attended by his granddaughter Rory. Richard suffered a bout of angina in December 2000. He has a serious second heart attack in 2006 and undergoes a open-heart surgery that'll leave him inoperative in his job for a good number of the following episodes.
During the time that Rory stayed with Richard and Emily so that she could have a "do-over", he was the first to admit and realize that "the moment they took Rory away from Lorelai, they lost."
Through the series Richard has adored Rory for her literary taste and sweet nature. He's very protective of her; as shown when he met Dean (her boyfriend during season 2). Richard grills Dean, knowing he's not good enough for Rory. During 'Richard in Stars Hallow' Dean gave Rory a car he made himself, Richard loudly protested (against Lorelai). The two males go to Gypsy's, she finds nothing wrong but Richard makes her check it many times. Dean says he loves Rory, Richard says she's young but doesn't hate Dean, somewhat apologizes for his interrogation. He notices Dean is tall, Dean sarcastically asks if he wants a dance, Richard says "No, thank you. I appreciate the offer though."
When Rory attends Yale, a Gilmore tradition, she enters a relationship with Logan Huntzberger. Richard is happy she's with a blue-blood but grieves when he learns Rory isn't a virgin.
In Season 7, while he was teaching an Economics class at Yale, he falls and has a heart attack. He is unable to fully function at his job after that.
- When he was a boy he loved to eat turtle neck soup. Nobody knows what it is.
- He also enjoyed Johnny Machete, a dish he prepares for Rory, Emily and Lorelai at one point.
- He got his first custom-made suit for his father's funeral. He never wore it again, telling his mother that he grew out of it.
- He was engaged to Pennilyn Lott, but ended up marrying Emily instead, much to his mother's chagrin.
- His father died when he was 10.
- His parents were second cousins.
- Rory is the apple of his eye, and at times she is all he can talk about.
- One of his hobbies is restoring vintage cars.
- He is secretly impressed with Lorelai, and helps her out whenever she needs it (i.e. with Rory's tuition, insurance issues at the Dragonfly, etc.)
- He was naked a full month his sophomore year at Yale and threatened with expulsion.
- He and his suite mates at Yale threw one of their suite mates out of the window, sandwiched in between two mattresses.
- He was on the fencing team at Yale.
- He went to the Bahamas for Christmas one year.
- When he was a child he used to love going on the roller coasters at Coney Island; he considered them to be faster as a child than as an adult.
- He once got so annoyed at street performers in Prague that he hummed Mozart's Prague Symphony to scare them away, and then kept humming it so that tourists would drop money at his feet. Two of them did, and he kept the money.
- When he was 27 he made a bad investment that could have cost him his home, his mother bailed him out. However he was able to repay her with in six months.