Real life effects of irresponsible actions
Gilmore Girls Season 5 is about finally getting what you want. Both Lorelai & Rory end up in relationships that have seemed fated for a long time. Both of the beloved Gilmore Girls will be faced with their dreams being different from reality.
Gilmore Girls Season 5 starts out with a feud between Rory & Lorelai. They have to deal with the aftermath of Rory sleeping with her married first love. As Dean's marriage falls apart Rory is only too eager to get back with him, only to find out that the relationship wasn't as strong as she had hoped. This season finally answers the question whether Rory & Dean are meant to be together.
Luke & Lorelai pursue their relationship. Since both parties have been confirmed bachelors & bachelorettes for years, it takes some adjustment to make their lives together work. Luke even has a "dark day." This isn't as dramatic as the previews made it seem. However, the lack of communication & willingness to open up will threaten the relationship time & again.
In the mean time Rory is intrigued by a secret Yale society of rich, irresponsible kids. It's in this group that she meets Logan Huntzberger. This is exactly the kind of guy that Emily Gilmore has always wanted for Rory. Will Rory stay true to her small town boyfriend or she will upgrade?
Emily & Richard have marital troubles during Gilmore Girls Season 5. They even separate at one point when Emily finds out that Richard has been having lunch meetings with his college sweetheart. Emily tries to date other men, only to realize that Richard is the one for her.
At Emily & Richard's vow renewal, things fall apart between the family. Emily tries to replace Luke with Christopher. Lorelai's attachment to her family eventually breaks her up with Luke. The usually independent, strong Lorelai is turned into a mess until she eventually finds her footing again as a single woman. Lorelai stops talking to her mother in retaliation for her failed relationship.
Gilmore Girls Season 5 is also a time for a juxtaposition of relationships. Things with Lorelai & Luke are repaired & stronger than ever. Luke is even trying to finagle an old house out of Taylor Doose's hands so he can live there with Lorelai. Rory in the meantime has to deal with her unstable love interest, Logan. She always wonders if he's being faithful or even if he's really her boyfriend. She takes an internship from Logan's father at a newspaper. Logan's family didn't initially accept Rory simply because of the humble life Lorelai has lived. Mitchum Huntzberger even tells Rory that she isn't cut out to be a reporter. Since this has been Rory's dream since she was a child, she is sent into a tailspin. She drops out of Yale & gets into trouble with the law.
At the end of Gilmore Girls Season 5, Lorelai approaches her parents for help. She tells them that she is worried about Rory & they need to present a united front to get Rory back into college. Emily & Richard agree & then go back on their deal when Rory shows up on their doorstep. They give her a place to live & Lorelai is furious that they are trying to turn her into the daughter they never had. As Lorelai's whole world comes crashing down, she goes to the only stable thing she knows: she proposes marriage to Luke. The season finale leaves us wondering if he will say yes.