After accidentally buying and wearing Luke’s ex-girlfriend’s sweater that he donated to the charity rummage sale, Lorelai learns from Sookie and Miss Patty that Luke had a “very serious girlfriend” called Rachel about five or six years ago (around 1995-1996), who broke his heart.
When Lorelai wonders how she could not have known about this relationship, or ever heard of Rachel before, the viewer can’t help but wonder too, as Lorelai has been in Stars Hollow since 1986.
Her friends explain that she was busy moving into her new house with her eleven year old daughter at the time, and that Rachel travelled a lot. As it doesn’t take that long to move into a new house, it makes you wonder how long this “very serious” partially long-distance relationship between Luke and Rachel lasted. Not very, by the sounds of it.
It’s a pretty lame explanation for why Lorelai’s never met or heard of Rachel before now, but at least tells us how long Lorelai and Rory have been in their home.