I have something embarrassing to admit. When I first started watching Gilmore Girls as a 12-year-old, I was Team Dean. I know, I know. I was young and naïve and completely fell for the “adoring boyfriend” trope that Amy Sherman-Palladino wrote for him. I could only hope for the kind of boyfriend who would notice what novel I was reading before we even met, get along with my mom, and build me a car. Don’t even get me started on the fact that he was 6 feet tall and had green eyes.
But rewatching Gilmore Girls this fall has me questioning everything I once believed about Dean being the perfect guy. The behavior I once thought was romantic now seems controlling and possessive, and even some of his sweetest gestures seem manipulative. Read on for Dean from Gilmore Girls’ biggest red flags that are impossible for me to ignore now that I’m watching the show as an adult.
He didn’t support Rory’s ambition
Rory’s entire personality in Season 1 revolved around wanting to go to Harvard and become a journalist, but Dean never fully got on board with that plan. He got short with Rory when she was swamped with homework or stressed about college applications, and he made her feel guilty whenever those things took precedence over watching a movie with him or going to his softball game.
It’s clear that Dean viewed Rory’s ambition as an inconvenience to him rather than one of her best qualities. This resentment never built into a huge blowout fight, but he gave plenty of eye rolls and passive-aggressive comments every time she prioritized school over him throughout their relationship.
He didn’t respect Rory’s independence
One of Dean’s more subtle red flags in Gilmore Girls is how often he disregarded Rory’s clearly communicated needs or beliefs. When she wanted a night alone to do laundry, eat Indian food, and have the house to herself, he immediately got upset and, of course, eventually showed up anyway. Similarly, when Rory shared that she felt The Donna Reed Show’s female stereotypes were outdated, Dean was weirdly defensive and seemed to prefer it when Rory dressed up and cooked him dinner.
The right person will understand that there’s nothing wrong with wanting alone time, having a different opinion, or pursuing a life that doesn’t look exactly like theirs.
He broke up with Rory because she didn’t say “I love you” back
I’ll give Dean major points for planning a romantic date for his and Rory’s three-month anniversary, but he ruined the moment by breaking up with her because she wasn’t ready to say the L-word. Rory was 16, in her first relationship, and clearly just needed time to process her feelings, but Dean (in typical Dean fashion) made it all about himself. Instead of giving Rory grace or listening to her, Dean snapped at her for not reciprocating his feelings when he wanted her to.
Watching this scene back as an adult, it’s hard not to notice how much unfair pressure that put on Rory. Love should never come with a deadline attached, and the fact that this was Rory’s first heartbreak says a lot about their relationship early on.
He called Rory 14 times in one night
At the time, I think the show wanted us to interpret this as Dean being genuinely worried about Rory or missing her. But now? Fourteen calls feel a lot more controlling than sweet. One of Dean’s biggest red flags in Gilmore Girls is definitely expecting Rory to answer him, no matter what her plans are.
Rory shouldn’t have to be physically and emotionally available to Dean every second of every day. She has school, her mom, friends, town events, books to read. But Dean’s need to constantly know where she is and what she’s doing makes it feel like he expects unlimited access to her time. The irony is that his 14 phone calls happened when he felt like he was losing Rory to Jess, but it was also this obsessive behavior that eventually pushed her away.
His jealousy was out of control
I’m not going to pretend Rory handled the Jess situation perfectly. She developed feelings for him while dating Dean, and she wasn’t honest about it. But Dean’s jealousy didn’t start with Jess. From the beginning, he seemed threatened by any guy who showed Rory attention.
At Chilton, he got into a fight with Tristan over his crush on Rory and continued to hate him until he moved away. Then, when Jess arrived in Stars Hollow, Rory spent half of Season 2 trying to prevent Dean from getting mad at her for simply talking to him.
Rory gave Dean real reasons to feel insecure once Jess entered the picture. But jealousy is still not an excuse to take your feelings out on your girlfriend or expect her to manage them for you. He made Rory responsible for constantly reassuring him, avoiding conflict, and proving that she wasn’t doing anything wrong.
He complained about participating in things that were important to Rory
Let’s give Dean his flowers by acknowledging that he showed up for Rory when she asked him to. He went to Friday night dinner; he took her to the Chilton winter formal; he escorted her to her cotillion; he went on a double date with Luke and Lorelai. But he also made it clear to Rory and everyone else how much he didn’t want to be there and had a bad attitude the whole time.
I hate to break it to you, Dean, but compromise is a natural part of any relationship. If every simple request your girlfriend makes of you feels like a chore, then you might be the problem. And for the record, you shouldn’t force your girlfriend to watch BattleBots for a month as payback for having to wear a tuxedo to her debutante ball.
He was a terrible husband to Lindsay
As a certified Rory hater, it pains me to say it, but she was right when she told Dean that he and Lindsay should continue dating instead of getting married. Dean married Lindsay even though he was clearly still in love with Rory (as evidenced by his behavior at his bachelor party) and seemed shocked that marriage isn’t always fun and easy.
Then, instead of being honest with Lindsay about not being happy in their marriage, he had an affair with Rory. He lied to Rory that Lindsay knew the marriage was over, slept with Rory, and then went home to Lindsay and took his frustration out on her.
Rory was in the wrong for getting involved with a married man, but Dean also could’ve ended his marriage before pursuing anything with Rory. Instead, he tried to have both, and Lindsay was left feeling humiliated.
Final thoughts
Looking back, I get why I was Team Dean when I first watched Gilmore Girls. He was cute, attentive, and completely obsessed with Rory. When you’re young, that seems like the ultimate romantic fantasy, but now I can see how Dean’s affection and attention turned into possessiveness, and his insecurity became Rory’s problem to solve.
Don’t get me wrong, Jess and Logan (and even Rory) have plenty to answer for too. But I think Dean is the boyfriend whose red flags become more obvious with age. He might have been Rory’s first love, but he definitely wasn’t the ideal first boyfriend that Lorelai led us to believe he was.
Christine Winder, Contributing Wellness Writer
Christine is a long-time reader turned contributing writer for the Everygirl. She has a BA in Communications from Roanoke College and lives with her two cats in Richmond, VA where she writes for several local publications.
