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Well, when you move a little to the left, you get the satisfaction of knowing you are doing something, but you are not pandering for a dog bone.
—Jason introducing Lorelai to his dog, Cyrus[src]

Jason Stiles is a principal character in Season 4 of Gilmore Girls. He is portrayed by Chris Eigeman.

Quick Answers

What is the relationship between Lorelai and Jason in Gilmore Girls? toggle section
In Gilmore Girls, Jason Stiles and Lorelai Gilmore, characters played by Chris Eigeman and Lauren Graham, share a complicated relationship. They knew each other from their teenage years at camp and reconnected when Jason and Richard Gilmore, Lorelai's father, became business associates. Their relationship began as a secret affair but ended when Jason sued Richard and Lorelai chose not to back Jason's lawsuit. They maintained a friendly relationship post-breakup, evident during Richard's 2016 funeral.
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Why did Lorelai and Jason break up in the series? toggle section
The breakup of Lorelai and Jason was prompted by a business conflict between Jason's father and Richard, Lorelai's father. When Jason's father threatened Richard's business, Richard made a deal excluding Jason. Jason's decision to sue Richard, and Lorelai's refusal to back him, led to their separation.
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What role does Chris Eigeman play in Gilmore Girls? toggle section
In the WB drama Gilmore Girls, American actor Chris Eigeman portrays Jason Stiles, who becomes romantically involved with Lorelai Gilmore.
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What is the significance of Jason's light sleeping habit in the storyline? toggle section
The light sleeping habit of Jason Stiles impacts his relationship with Lorelai, as he requires solitude for sleep, leading Lorelai to sleep in a guest room. His preference for quiet is also seen in his choice of pet, a dog named Cyrus, known for its remarkable stillness and silence.
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What is Jason's role in his father Floyd Stiles's company? toggle section
Jason Stiles, also referred to as Digger, was poised to inherit his father Floyd Stiles's insurance firm. In 2003, he departed from the firm to establish a new business with Richard Gilmore. This transition involved Jason transferring some clients from Floyd's firm to their new venture, resulting in Floyd initiating a lawsuit against Jason and Richard's company for client theft.
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Character[]

Jason is, in a sense, an exaggerated male version of Lorelai. They both share a similar sense of humor, and he is very "off center", as Lorelai at one point describes it to Rory. Jason has worked at his father, Floyd Stiles's, company since he was very young and is a Harvard graduate.[2] Jason at one point reveals to Lorelai that he is an extremely light sleeper and cannot sleep with anyone else, and Lorelai has to sleep in a guest room, which houses his "distractions" like films and books. He has a very unusual dog named Cyrus, which has the ability to stay remarkably still without moving and making any noises, which is what Jason loves about him.

Story[]

Jason is Richard's business partner through Season 4. He also dates Lorelai, making him her last boyfriend before she begins dating Luke. Jason initially teams up with Richard in the hopes of trying to defeat his father's company. However, Jason has a huge falling out with Richard after Jason's father, Floyd Stiles, threatens to destroy Richard's business. Richard, in turn, makes a deal with Floyd that leaves Jason out in the cold. Jason sues Richard, which prompts Lorelai to break up with him. Jason is seen one last time at the Dragonfly Inn, trying to reconcile with Lorelai, which fails.

Relationships[]

Floyd & Carol Stiles

Jason has a passive-aggressive antagonistic relationship with his father, whom he usually refers to as Floyd. Although he does call him Dad when he furiously races after Floyd following the latter's proclamation that he is suing Jason and Richard's company. Jason's mother, Carol, appears somewhat passive in her one appearance, although Jason mentions several times to Lorelai that he speaks to his mother. Jason never refers to her by her first name, although he does not speak of her with respect either, mentioning to Lorelai that she takes 'happy pills' and insinuating the pills make her unable to converse at her normal standard.

Richard Gilmore

Jason seems to respect Richard's business fervor and shows loyalty to Richard over his own father. Richard entertains the idea of Jason's business while Emily is indignant at Jason's relationship with his family, and Richard seems to like Jason, yet is not hesitant to sell Jason out once his and Emily's livelihood is endangered, effectively ending their business and social relationship.

Lorelai Gilmore
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They meet as kids at summer camp and while canoing, Jason apparently stands up to tip Lorelai into the water to make her shirt see-through. Such a gentleman. While it's not certain if Digger is a name Jason sustained at camp, he does call Lorelai by her camp name (assumably) when they meet in 2003 as adults. Jason is immediately crass about Lorelai's looks, and obviously infatuated and pursues her for a date.

Lorelai is hesitant because Jason belongs to the world of riches she wants to leave behind, but agrees after a nasty confrontation with her mother, to go on their first date. As they continue to date, Jason wants to announce it to Emily and Richard, but Lorelai is afraid of letting her parents into her personal life. Jason has trouble with this, but agrees to appease her. While Lorelai states on many occasions she finds Jason weird, they have a rhythm that both enjoy and perhaps Jason is a bit more committed to their relationship than Lorelai is.

Quotes[]

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Richard – You hate your father that much?
Jason – I don't hate him. I just don't wanna be him

Trivia[]

  • Jason went to Harvard, although his father, like Richard Gilmore, is a Yale alumnus. This is similar to Lorelai's approach to discern her life from that of her parents.
  • Jason has at least one sibling, during the Friday Night Dinner in Tick, Tick, Tick, Boom! it is mentioned that he has a nephew.

Episodes[]

SEASON 4 (13/22)
03. The Hobbit, The Sofa and Digger Stiles
05. The Fundamental Things Apply
06. An Affair to Remember
08. Die, Jerk
09. Ted Koppel's Big Night Out
10. The Nanny and the Professor
12. A Family Matter
13. Nag Hammadi Is Where They Found the Gnostic Gospels
14. The Incredible Shrinking Lorelais
16. The Reigning Lorelai
17. Girls in Bikinis, Boys Doin' the Twist
18. Tick, Tick, Tick, Boom!
19. Afterboom
22. Raincoats and Recipes
A YEAR IN THE LIFE (1/4)
01. Winter

Notes and references[]

  1. The Hobbit, The Sofa and Digger Stiles — Richard mentions that Jason is 37. He is either from 1965/1966
  2. The Hobbit, The Sofa and Digger Stiles