Christopher and Lorelai met at the age of 6, were best friends in adolescence and dated. After Lorelai got pregnant and had Rory, it is presumed, though never shown, that she and Christopher broke up. Around the start of the series, Christopher is sporadically in and out of their lives; sometimes several years span between his appearances. Eventually, he becomes more responsible and shows up at important moments in Rory's life, later rekindling his romance with Lorelai, which is halted by his girlfriend's pregnancy.
When Sherry leaves Christopher to raise Gigi alone, Lorelai helps him out, much to Rory's dismay, and Emily encourages Christopher to go after Lorelai while Lorelai is with Luke. This puts a long pause on Christopher's connection with the Gilmores, but he resurfaces offering to pay for Yale. When Lorelai breaks up with Luke, she ends up in bed with Christopher and they eventually start dating and are later married. Their marriage ends with both ceding that maybe they were never meant to be.
Born into families of very similar economic advantage and social conduct, Lorelai and Christopher seem to bond over their mutual inability to see a future for themselves within the confines of the expectations that come along with this lifestyle. Add to this that their parents were good friends, leaving Christopher and Lorelai with a lot of opportunities to spend time together. Entering their teen years, Lorelai one day kisses Christopher, saying she 'just wanted to know what it would feel like', which Christopher later recants to Rory as the best day of his life.
Presumably shortly after this they start a relationship in high school and start having sex as Lorelai gets pregnant around the time of her coming out. While it may just be a relationship of youth, Christopher later in life seems to have idealized their connection and consideres Lorelai his true love. After Lorelai decides to keep the baby (also her parents would not let her get an abortion), she lives with Richard and Emily for a year before leaving home, and it is unknown whether or not she and Christopher remained a couple, but unlikely due to the wrath of their parents and Lorelai's departure from Hartford.
After Lorelai leaves for Stars Hollow, Christopher is only sporadically in and out of his daughter's life until she's 17, for reasons unknown. He states at one point that it's hard for him to see Rory because he misses her so much it's easier on him to stay away. Lorelai is angry with Christopher for never showing up for her, and his daughter, but their abrupt separation years before leave their relation lingering in their teen years, with both of them returning to a version of their teen selves around one another.
Their relationship as adults is built around whether or not Christopher can be a stable force in Rory's life – and Lorelai's, as something akin to a husband. With their relationship as described above, this is not a snap transition and it is only when Christopher gets his life on track and moves toward happiness that Lorelai is willing to give it a go.
Seeing Christopher getting serious with Sherry leaves Lorelai heartbroken, and she realises that she may have been waiting for him since they were 16 to become a man she could rely on, as Rory's father and maybe Lorelai's husband. Christopher is deeply hurt by Lorelai confessing this, yelling at her and leaving, but Lorelai, with this newfound realisation, is not seen diving into dating even though she now allegedly is emotionally relieved of the subconscious idea of her and Christopher as her future – especially given the seriousness of his relationship with Sherry. Instead, as Christopher's increasingly showing up for Rory, Lorelai keeps her romantic focus on him. Whether this is the reason for Christopher slowly retreating from his commitment to Sherry is unknown, but plausible. When he tells Lorelai that his relationship isn't going well anymore, they soon start anew – as adults – and decide to embark on a committed relationship. Their happy reunion is woefully cut short when Christopher discovers that Sherry is pregnant — and intends to keep the baby. With a broken heart Lorelai sends Christopher off to a future with Sherry, as Chris asks her to 'break the news' to Rory.
Although ecstatic at the chance to show he can be a good father, Christopher is also heartbroken at having to leave Lorelai. His sorrow extends to a furious Rory, who refuses to talk with him, and the whole mess is incredibly hard on Lorelai. She encourages Rory to be a part of the process, however, to ensure a good relationship between Rory and her half-sister. Unfortunate circumstances see Lorelai invited to Sherry's baby shower, where Sherry promptly thanks Lorelai for having supposedly 'saved' Sherry and Christopher's relationship, unknowingly salting the wound in Lorelai's heart. To make matters worse, Lorelai ends up having to be present at the hospital for the birth of Christopher's daughter, for Rory's sake. Following these events, Lorelai slowly lets herself move on and embarks on a light, but caring relationship.
Two years later, she receives a distress call from Christopher and finds that Sherry has left him and her daughter, Gigi. Although in no way indebted to the, at this point, wayward presence Christopher has become in her life, she helps him out.
Notes and references
- ↑ 1.0 1.1 1.2 1.3 1.4 Christopher Returns
- ↑ 2.0 2.1 2.2 Presenting Lorelai Gilmore
- ↑ 3.0 3.1 It Should've Been Lorelai
- ↑ 4.0 4.1 Teach Me Tonight
- ↑ 5.0 5.1 I Can't Get Started
- ↑ 6.0 6.1 Norman Mailer, I'm Pregnant!
- ↑ Come Home
- ↑ 8.0 8.1 Wedding Bell Blues
- ↑ He's Slippin' 'Em Bread... Dig?
- ↑ Partings
- ↑ French Twist
- ↑ Farewell, My Pet
- ↑ 13.0 13.1 13.2 13.3 Dear Emily and Richard
- ↑ Haunted Leg
- ↑ Take the Deviled Eggs...
- ↑ Lorelai Out Of Water
- ↑ Gilmore Girls: Lauren Graham reveals season 7 plot she forgot (November 2016)