‘Gilmore Girls’: The Affair With Dean and 3 Other Times We Couldn’t Stand Rory

Lorelai Gilmore (Lauren Graham) and Rory Gilmore (Alexis Bledel) will always have a special place in our hearts, but that doesn’t mean they didn’t bother us at all during Gilmore Girls‘ seven-season run or its 2016 Netflix revival, Gilmore Girls: A Year in the Life

We’ve already established Lorelai as a not-so-great character. And Rory had her faults, too. Sure, TV characters aren’t supposed to be perfect. But there were times when we couldn’t stand Rory for some of the decisions she made.

Alexis Bledel and Lauren Graham in 'Gilmore Girls'
Alexis Bledel and Lauren Graham in ‘Gilmore Girls’ | Mitchell Haddad/CBS Photo Archive via Getty Images

1. When Rory didn’t want to admit she had feelings for Jess

In Gilmore Girls Season 2 a love triangle started to form among Rory, Dean Forester (Jared Padalecki), and Jess Mariano (Milo Ventimiglia). Rory got to know Jess, Luke Danes’ (Scott Patterson) misfit nephew, and liked his mysterious, bad boy ways. They especially bonded over their shared love of reading.

Meanwhile, Rory had been dating Dean. And whenever Dean and Rory crossed paths with Jess, it became obvious that Rory had developed feelings for the new kid in town.

To make the situation worse, Rory dragged out her relationship with Dean, not wanting to admit she liked Jess. Dean became paranoid, and everything came to a head when he broke up with Rory at the Stars Hollow dance marathon.

2. Rory had an affair with Dean 

This one stands out as probably the worst decision Rory ever made. After she got weird about Dean getting married so young, Rory and Dean wound up having an affair.

If that wasn’t bad enough, Rory got mad at Lorelai when she approached the situation logically and reminded Rory that Dean hadn’t actually separated from his wife when they started their affair. Rory ended up running away from the whole situation and spending the summer in Europe with her grandma, Emily Gilmore (Kelly Bishop), while she and Lorelai remained at odds about the affair. 

3. Rory later had an affair with Logan

Rory developed a track record as a serial cheater during the show’s original run that became a continuing theme in the Netflix revival. While fans were excited to see Logan Huntzberger (Matt Czuchry), Rory’s college boyfriend, in Gilmore Girls: A Year in the Life, they were less than pleased to find out his storyline involved an affair with Rory.

Despite Logan being engaged to another woman and Rory having a boyfriend, they decided to rekindle their college romance. What made us really question Rory’s judgment here — besides the fact that she decided to have another affair — is she had turned down Logan’s marriage proposal at her college graduation. She had the chance to be with Logan and didn’t want it, only to have an affair with him several years down the road.

Alexis Bledel and Matt Czuchry in 'Gilmore Girls: A Year in the Life'
Alexis Bledel and Matt Czuchry | Saeed Adyani/Netflix

4. Rory left Yale because her skills as a journalist were criticized 

Remember when Rory interned with Logan’s publishing tycoon father, Mitchum Huntzberger (Gregg Henry)? And she loved every second of it until Mitchum told her she “didn’t have it” as a journalist? Mitchum’s criticism was harsh, but Rory should’ve brushed it off and worked harder to prove him wrong.

Instead, she stole a boat and ended up dropping out of Yale. When we watched this play out the first time we wanted to reach through our TV and give Rory a boost of confidence. After all, she had been valedictorian at her competitive high school and did well at Yale. If anything, she should’ve taken Mitchum’s advice as a reminder to take risks, even as an intern. 

If a second Gilmore Girls revival happens, we expect Rory to make some bad decisions. But we hope she doesn’t have another affair or doubt herself or her abilities like she has in the past.