"Gilmore Girls" is infamous for creating characters that are a little too perfect. In an otherwise fantastic show, that tends to be everyone's one complaint. The characters—mainly the two main characters—appear a little too perfect in the first few seasons that people began to lose connection with the characters. To retro-act this mistake, the writers make the characters act so out of character to do something imperfect so people begin to connect with the characters again.
In the first couple seasons, Rory Gilmore's life seemed a little too perfect. She was going to a prestigious prep school where she was excelling, she had the perfect boyfriend who would do practically anything for her, and the one person that was trying to ruin her relationship, and her life, had just been shipped off to Tree Hill—I mean, military school. Her life had everything it needed, nothing more.
Then Jess showed up. Don't get me wrong, I love Jess and the two of them together, but he was originally only introduced to create tension in an otherwise perfect life. Rory ends up falling in love with Jess while still dating her loyal Dean. She strings the poor boy along for almost two seasons before he finally gives up and then she goes straight into dating Jess. The writers couldn't justify allowing their main character to go on leading an absolutely perfect life because no one can relate to it.
They repeat this with Rory many times throughout the original series. They make her have an affair with Dean, her married ex-boyfriend, steal a boat simply because she was told that she "didn't have what it takes" to become a journalist and, to top it all off, she drops out of college and stops talking to her mom. Then, in the revival, she is having an affair with her college ex-boyfriend who is engaged.
The only other character that the "Gilmore Girl Complex" seems to affect is the older Lorelai. They paint her parents in this horrible light to make her seem like this poor, helpless child when she is actually a full-grown adult. Lorelai falls in love with one of Rory's teachers in one of the first seasons of a show and, when he proposes in the middle of a fight, she tells him that it isn't right and it's not enough to constitute a proposal and that there needs to be "like a thousand yellow daisies."
So, what does he do? He gets the flower shop to deliver a thousand yellow daisies to her work. He never pushes her about it and lets her take her time to decide. She decides she wants to get married, plans the whole wedding and then decides she doesn't want to get married anymore and runs away. Doesn't try to talk to him, doesn't say "I thought I wanted to do this and now I don't, sorry," she just runs away.
Later in the series, she gets together with Luke, which the whole series was leading up to. They date, move in together, fall in love, the whole gamut. Then Chris (Rory's father and Lorelai's ex-boyfriend) dad dies and she has relationship problems so she goes running to him and they sleep together. So when Luke shows up to rectify his relationship problems with Lorelai (because he just found out he had a kid and needed some time before he ran off and got married to Lorelai), she tells him and he gets mad—rightfully so.
Lastly, let's talk about Lorelai and Chris. Any time Lorelai is single for any period of time longer than 5 episodes, she goes running back to Chris. They fall in love again and then something (a pregnant ex-girlfriend, a kid, Luke, Rory, Lorelai's parents, you name it) gets in the way and they break up. But it's okay because in half a season, after Lorelai has dated and broken up with someone else, she'll be back with him.
Don't get me wrong, "Gilmore Girls" is a show that will forever hold a special place in my heart, but the writers have a problem of creating characters that are too perfect for the general public to relate to. Then, they believe they can fix this just by making them mess up on an astronomical scale. This isn't how real humans work, but I guess it's how fictional characters work.