Lorelai was born to the esteemed Richard and Emily Gilmore. She grew up with a rich lifestyle, but she also felt very caged by her parents. More so by her mother. She did not wish to follow the path that they wanted for her, but she wanted to do her own thing. She was rebellious against them growing up, even more so as a teenager. She and her mother rarely saw eye to eye and her father was out of the house so often that it didn't matter much there, but she always felt a disappointment to him. 

Lorelai has known Christopher Hayden since they were young. They are often thrown together during events and it's when they're teenagers that they grow even closer. So close that Rory ends up pregnant and even though Christopher proposes, she runs away. She never wanted to be forced into decisions that are against her will, something she's hated from growing up in her parents household. 

She runs to Stars Hollow, a town not too far from Hartford. It's small and quaint and she's alone, but soon meets Mia who takes her in with open arms. Mia gives her a place to live and hires her as a maid at the Independence Inn. It's at the inn where Rory grows up and where she saves enough money to get them a house of their own. 

Mia eventually hires her on to help run the inn and Lorelai does it well. She and her best friend Sookie, who works at the inn with her, decide that they want to one day run their own inn and when the time comes for it, they find a cute place and name it the Dragonfly Inn.