- ❝ Christopher – Only took me ten years and several failed business ventures to figure out what I wanted
- Lorelai – Which is?
- Christopher – Not my parents' life ❞
Rory's father and Lorelai's high school boyfriend. He and Lorelai tried to start a relationship as adults several times, but the timing was always off. They do end up getting married spontaneously on a trip to Paris, but they separate (on good terms) only a few months later as Lorelai realizes they weren't right for each other. Christopher knew Lorelai is still in love with Luke and decide to step aside. He was previously engaged to Sherry, with whom he has a daughter, Gigi.
Christopher grew up surrounded by family wealth on the same scale as the Gilmores. He does not seem to have a very loving relationship with his parents Straub and Francine, who respectively expect only business success from Christopher or criticise everything about him. While he didn't express great love for his grandfather Hayden, the latter was most fond of Christopher out of the entire family and so, Chris may have had at least one pleasant relationship with someone in his family that wasn't based on status and image.
Following the pregnancy, Christopher sheepishly complied with his parents' wishes that he marry Lorelai, live at the Gilmore house and work at Richard's firm, although thanks to Lorelai's strength of will this never occurred. While Chris is shown to have had limited contact with Lorelai and Rory in the years that followed, he never did attend Princeton as he parents wished for him, and it is unclear whether he did take up academia.
Christopher was never really sure how to handle Lorelai's falling out with and leaving her parents, resulting in him not handling it at all and thus being mostly absent from Rory's life. Christopher comes to Stars Hollow for the first time when Rory is 16, and although established that Rory does have a relationship with her father of sorts, Lorelai is wary of him getting to close to their daughter if he's not going to be a constant presence in her life. Christopher does keep in touch with Lorelai and Rory for a long time. Chris admits to Lorelai that it's heartbreaking for him to see Rory, because he misses her so much all the time that it's 'easier to stay away'.
Chris proposes abruptly to Lorelai during a conversation about their previous night together and Lorelai lets him know that he might have a chance one day, when he's ready to be a father and husband. For about six months Chris is not around, although he seems to have taken up a frequent habit of phoning Rory, which later turns into a weekly occurrence. When Lorelai calls him up on the eve of her bachelorette party, telling Chris for the first time that she's getting married, he knows that Max is the guy, courtesy of his chats with Rory. When Chris makes his second visit to Stars Hollow, Lorelai discovers that he got a steady job, a car, a new phone number and apartment – in Boston. He isn't overly passionate about his work, but seems happy to have a steadiness in his life and relays to Lorelai that he doesn't want his parents life. This could mean that he doesn't want to focus on his reputation and how his career defines him, as his parents are defined by their 'societal stature' and riches.
Chris later returns to Stars Hollow to present Rory at her debutante ball and tells Lorelai that he is now living in Boston with his girlfriend Sherry Tinsdale and has a good job. When Rory and Jess crash Rory's car and she fractures her wrist, Christopher is the one Lorelai calls after seeing Rory's damaged car and he ends up staying with them for a couple of days. At first Sherry and Christopher are serious, but Chris later becomes unhappy with Sherry, wanting to leave her and he and Lorelai sleep together. However, when he learns Sherry is pregnant, he goes back to her. Sherry gives birth to their daughter Georgia, nicknamed Gigi. 2 years later Sherry leaves him and Gigi to take a job in Paris. Christopher repeatedly turns to Lorelai for help with his daughter. Christopher's presence in Lorelai's life puts strain on her relationship with Luke Danes. Lorelai stays over at Christopher's house the night she and Rory find out from Richard and Emily that Christopher's father, Straub Hayden, has died, and the both of them drink tequila all night long, but have no sexual interaction whatsoever. At Emily's urging, Christopher attends Emily and Richard's wedding vow renewal and begs her to get back together with him. Lorelai is furious with both her mother and Christopher, and they don't speak for several months.
They get back in touch when Christopher wants to financially provide for Lorelai and Rory, and they agree he'll take over paying Rory's tuition at Yale. After Lorelai and Luke break up, Lorelai spends the night with Christopher, and they begin a relationship. After accompanying Gigi to France to see her mother, Christopher asks Lorelai to marry him and elope, and Lorelai and Christopher spontaneously get married, and Christopher moves into Lorelai's house in Stars Hollow. However, Christopher continues to be very jealous of Luke. After he finds a letter that Lorelai wrote for Luke's custody battle, Christopher questions whether Lorelai really loves him. When Lorelai's father has a heart attack, Christopher is upset to see Luke at the hospital. Lorelai considers cutting Luke out of her life completely to save her marriage, but a conversation with Sookie makes Lorelai realize that their relationship isn't right. She tearfully breaks up with him and he sadly (but respectfully) realizes that if it took her 20 years to get him to say "Yes", he should have known they weren't meant to be. They part on good terms and Chris is seen proudly watching his daughter graduate from Yale.
Main article: Lorelai and Christopher
Chris and Lorelai have known each other since age 6 and were best friends growing up. Like Lorelai, Chris comes from a privileged family and was unhappy with the life his parents had planned for him. At the age of 14, Lorelai walked over to him and kissed him in the school parking lot "Just to see what it felt like".
He spent many times after school hanging at Lorelai's, where the two would search for naked people on the balcony. Rather than go to Princeton as his parents wanted, Chris wanted to travel through Europe with Lorelai after high school. When Lorelai became pregnant, Chris agreed to get married and work for Richard's company, as their parents wanted; however, Lorelai refused. Lorelai raised Rory alone, and Chris had limited contact with his daughter.
Having been a flakey presence in Rory's life until she turns 16, they don't know each other that well. The first time Chris ever visits Stars Hollow, Rory is deliriously happy that he's there, and her joy at seeing her dad continues for about a year. When Chris and Lorelai nearly reunite, he promises Rory that they will be a family, and when everything falls apart, Rory's view of her father is altered. They eventually get back in touch and Rory does attend the birth of her sister on amicable terms with her father, yet, when at college, she relays to Marty how she doesn't know how to feel about her dad because she can't count on him. This emotion stays with Rory and is exacerbated when Christopher elicits Lorelai's help after Sherry leaves him to raise Gigi alone. The two are at odds, Chris demanding Rory respect her father and Rory refusing to accept his friendship with Lorelai, but their feud ends when Rory learns that her estranged grandfather, Straub, has died. Christopher has a great relationship with Rory and always keep in touch.
Christopher's relationship with his parents is strained at best, similarly to Lorelai's with her parents. Straub talks over his head and embarass him in front of other people with no pause, and his mother constantly corrects his behaviour. It is indicated by their appearances that the two are emotionally constipated people who have subjected Christopher to emotional abuse his entire life, thus providing him with incredibly low self-esteem. Once Gigi is born and Chris becomes a single parent, his relationship with his mother seems to better, as Francine is often said to be looking after Gigi. His relationship with Straub, however, remains cold until Chris's father dies in 2005.
- Hey. Nice shirt. Take it off
- – That Damn Donna Reed
- The Offspring is his favorite band in 2001.
- His first kiss was with Lorelai in the school parking lot at the age of 14.
- He crashed his new Porsche two hours after receiving it on his 16th birthday, with Lorelai next to him.
- He proposed to Lorelai three times .
- He has known Lorelai since they were both 6.
- He is the only one who calls Lorelai "Lor".
- Lorelai confessed to Sookie that all her 'bad girl' moments were with Christopher.
- Jackson Belleville thinks he looks more like George Clooney than Brad Pitt, and Andrew thinks he looks like Billy Crudup.
- He can play the opening lick to Smoke on the Water and Jumpin' Jack Flash on guitar.
- He owns/owned a red 2000 Indian motorcycle.
- Jess was the only boyfriend of Rory's he didn't meet, but he jokingly threatened to rip his head off after Rory and Jess got into a car accident.
- He got along fine with both Dean and Logan.
- Christopher is a nice guy and just like Lorelai, he is also childish and can never grow up.
- Unlike Emily and Richard who has strings attached when they had to pay for Chilton and Yale, He gave Rory no strings attached and Rory has a good relationship with that.
- Christopher and Lorelai never regretted having Rory in their lives. Christopher never wanted his father's life or go to Princeton University.