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. In season 7, 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 1.10. He had a serious second heart attack in To Whom It May Concern and in 7.13 he 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 Lorelei, 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 mock turtle soup.
- He got his first custom-made suit for his father's funeral. He never wore it again, claiming 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.
- 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 somewhat close with Lorelai, and helps her out whenever she needs it (i.e. with Rory's tuition, insurance issues at the Dragonfly, etc.)
- Chilton is only five minutes away from his residence.
- He was on the fencing team at Yale.
- He went to the Bahamas for Christmas one year.
- At times he is overly sensitive.
- 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 they were 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.