Lorelai Victoria Gilmore was born to a life of privilege. Her parents, Richard and Emily, had high expectations for her but being the free spirit that she was Lorelai shunned that. When Lorelai was sixteen years old she found herself pregnant by Christopher Hayden. Their parents insisted the two get married and Christopher work for Richard's company. Lorelai knew, though, that if they did that they'd never get to realize their dreams and she refused to marry him. She gave birth to her daughter, naming her after herself - Lorelai Leigh Gilmore, known as Rory. At first Lorelai and Rory lived with her parents but without letting Richard and Emily know, they moved out leaving only a note when Rory was about a year old. They settled about twenty miles away in Stars Hollow. Lorelai found a job as a maid at the Independence Inn and she and Rory lived in the grounds until they were able to afford their own house. In Stars Hollow they were surrounded by colorful characters like Miss Patty, Babette, Kirk and diner owner Luke. As the years went on Lorelai worked her way from maid to the point where she was running the inn. Rory began high school at Stars Hollow High, but in her sophomore year she was accepted to Chilton, a prestigious school in Hartford, the same city where Richard and Emily lived. Unable to afford the tuition on her own, Lorelai was forced to swallow her pride and ask her parents for help. They agreed but on the condition that every Friday night Lorelai and Rory come to dinner, thus beginning to repair Lorelai's fragile relationship with her parents. Lorelai also began dating Rory's English teacher Max Medina. Things turned serious and the two became engaged but just days before the wedding Lorelai backed out. Lorelai reconnected with Rory's father Christopher again, but things ended when his girlfriend got pregnant. Lorelai and her friend Sookie, the chef at the inn, longed dreamed of owning their own inn. When the Independence Inn had a fire and did not reopen they took their chance and began working on the Dragonfly Inn. While work was being done, the two had their own catering business. Lorelai also began dating her father's business partner Jason Stiles, but the two kept the relationship a secret from their parents. As their relationship was ending and the Dragonfly was nearing completion, Lorelai was getting closer to Luke. The relationship the two had danced around for nine years was finally beginning. The two began dating, but when Emily invited Christopher to her vow renewal ceremony since she believed Luke wasn't good enough for Lorelai, the two broke up. They soon patched things up and Lorelai proposed to Luke when Rory dropped out of Yale and betrayed her by going to Richard and Emily for help. While separated from Rory, Lorelai got herself a dog who she named Paul Anka. Lorelai and Rory patched things up, but her engagement with Luke was put on hold when he learned he had a daughter from a previous relationship. Emily and Richard, however, finally accepted that Lorelai was going to marry Luke by planning to buy the couple a larger home in the Stars Hollow area. Due to the strain caused by Luke hiding his daughter from Lorelai, the two broke up. Lorelai rebounded by sleeping with Christopher and they began dating again. On a trip to Paris to take Christopher's daughter Gigi to her mother, Lorelai and Christopher eloped. They returned to Stars Hollow and Christopher tried to adjust to life there. When Luke was going through a custody battle with his daughter April's mother, Anna Nardini, he asked Lorelai if she would write a character reference for him. Despite things being awkward between the two of them, Lorelai wrote a very long letter in which she expressed what a good man she believed Luke to be. Christopher found the letter and became very jealous. After a fight with Lorelai, he ran off for a bit and stayed away, even when Richard Gilmore suffered a heart attack. When Christopher did return, Lorelai decided she could not continue their marriage. She wanted it to have worked, but it didn't. Lorelai began to rebuild her friendship with Luke. A very proud Lorelai watched as Rory graduated from Yale. The town of Stars Hollow threw Rory a large going away party in the middle of town, organized by Luke. When Lorelai found out, she kissed Luke. Lorelai and Rory enjoyed early morning coffee at Luke's one last time before Rory left Stars Hollow for her first job as a journalist.