In season 1 Rory gets accepted into Chilton and Lorelai asks her grandparents to help pay for Rory breaking no contact with them for the first time in years. Rory also finds a new boy that she likes named Dean and she starts dating him for a while. This season is the start of Rorys school career and is the intro to boyfriends in the show. Lorelai also gets engaged by her boyfriend Max Madena and they have yet to plan their wedding.
In season 2 Max and Lorelai break off their engagement because Lorelai cant get the through out of her head that its meant to be Luke. A new character also get introduced name Jess. Jess is Luke's Nephew that constantly flirts with Rory. This starts a on going problem between Jess and Dean that last throughout the show.
In season 3 Rory starts to become much more friendly with Jess which causes Dean and Rory to break up. Devestated, Rory continues on in her senior year of Chilton exploring colleges deseding between her mothers choice of Harvard and making her grandfather happy and going to Yale.
In season 4 Rory starts her first year in college. Over whelmed she gets back together with her ex-boyfriend Dean breaking apart his marriage. Lorelai also begins to open a hotel called the Butterfly Inn located in a nearby town after being the manager for another hotel for many years. She decided to work with her best friend Sookie and build a new hotel with her, Sookie being the cook and Lorelai being the manger.
In season 5 Rory meets a boy at school named Logan. They soon begin to date, but when his grandfather, the head of the newspaper at Yale tells Rory she lacks the quality's to be a journalist she drops out of college just to return only a few episodes later. Meanwhile Lorelai and Luke begin a relationship taking off very fast.
In season 6 Lorelai struggles with her engagement with Luke because of a big secret he has been keeping between them of his daughter April. Meanwhile Rory moves in with her grandparents and joins the DAR, Daughters of the American Revolution. Lorelai is not sure how to deal with this because she does not want her daughter to have to go through what she went through many years ago and starts a learning curve for both of them.
In season 7 Lorelai cannot bear the though of Luke keeping secrets from her during their relationship so they break up and Lorelai goes back to her ex-boyfriend and Rory's dad, Christopher. Rory graduates college and finds her way in life while stilling dating Logan. Lorelai and Christopher soon break-up again leaving Lorelai single he end of the show and Rory in a situation ship with Logan due to complications of her dropping out and coming back to Yale.
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