Over the course of the series, it becomes clear that Rory systematically avoids any relationship that has the potential to really last. She literally always picks the flighty bad boy over the stable nice guy, flips out when any boyfriend gets to serious and finally breaks up with Logan when he proposes to her. On the surface, this just seems like she has to maintain her 'independent woman' status. But consider, girls innately tend to see their mothers as models for what they should be and their fathers as models of the boys they should pursue. Rory plays this for all it's worth, basically being a miniature version of her mother. So what does she take from her father? It's pretty clear that Rory unconsciously absorbed the idea that the proper role for a romantic partner is to hang around for a while, and then leave. In her mind, a key attribute for a man is "not there anymore."