Rory and Dean may have seemed like the picture-perfect teenage couple in Rory and Dean's relationship timeline is when they sleep together while he's married to Lindsay — and yet, Rory still can't come to grips with the notion that he is no longer "my Dean."

But while Rory may not have a clear grip on the situation when it comes to Dean, she is laser-focused on her educational and career ambitions throughout Gilmore Girls. ed by Lorelai and her grandparents, Rory has dreamed of being a journalist since she was a little girl, and is determined not to let anything get in her way. Rory even turns down Logan's marriage proposal at the end of Gilmore Girls because she wants to prioritize her professional future. These life goals are a lot different than Dean's, and therein lies the problem of his and Rory's relationship.

Gilmore Girls Confirmed Rory & Dean Weren't Endgame With "That Damn Donna Reed"

Their Core Values Are Too Different

At the beginning of Gilmore Girls season 1, episode 14, "That Damn Donna Reed," Rory and Lorelai are watching The Donna Reed Show when Dean comes over. The Gilmore girls are yukking it up, cracking jokes about the exaggerated stereotypical gender roles the '50s sitcom is enforcing, but Dean has a different take. He embraces the idea of a nuclear family, and thinks it's sweet that Donna Reed's character finds fulfillment in cooking dinner for her husband and being a homemaker.

Dean's perspective goes far beyond a TV show, and he's emphatic that this is what he values in life, too, frequently talking about his own mother in the same idealistic way he spoke about Donna Reed. He's completely ignorant of the legitimate arguments Rory presents him with — that shows like The Donna Reed Show reinforced oppressive gender stereotypes for women. This essentially proves why Dean and Rory could never work, as he dreams of the picket fence life. which is the last thing that she wants.

This Gilmore Girls Episode Was A Clear Sign Rory & Dean Didn't Want The Same Things

Dean Misses The Point Of Rory's Theatrics

After Rory and Dean's argument about The Donna Ree Show and gender roles ends in a stalemate, she decides to dress up like a 1950s housewife and cook Dean a steak dinner to show him how ridiculous his standards are. However, her playing house charade ultimately backfires when he takes her theatrics seriously, finding it endearing that she went to all this trouble to make his fantasies come true.

If Dean had his druthers, Rory would be wearing an apron and cooking for him every night.

If Dean had his druthers, Rory would be wearing an apron and cooking for him every night. But that's not who she is, nor who she'll ever want to be. Rory is someone with an unquenchable thirst for knowledge, someone who wants to learn and grow. In fact, Rory's biggest takeaway is her discovery that she grossly underestimated Donna Reed, who was an uncredited producer and director on her own show, making her one of the first women TV executives.

This is what Rory latches onto and ires, and we see her eyes light up at sharing the knowledge with Dean. In that regard, Rory really does want to be like Donna Reed, but all Dean takes away is that his girlfriend acting like a domestic goddess was a positive experience for her.

Dean Got What He Wanted In "That Damn Donna Reed" & Still Threw It Away

Lindsay Was Ready To Be Dean's Donna Reed

Ultimately, Rory didn't succeed in winning her argument with Dean, as the whole storyline ends with her doing the dishes while he takes out the trash. Dean is tickled pink at getting to play "man of the house", and that is precisely what makes him such a toxic boyfriend. He shouldn't be thrilled that Rory changed for him, he should want her to be herself — and if who Rory is isn't compatible with what Dean seeks in a partner, he should look elsewhere and not put that pressure on her.

I was actually happy when Dean first started dating Lindsay in Gilmore Girls because they seemed like such a better match than him and Rory. Lindsay is a sweet girl next door who wants a simple life in Stars Hollow, and it looks like they'll live happily ever after when they get married. But Dean's inability to get over Rory and the startling realization that — gasp! — being the sole income earner in a household is tough, sees him turning his back on the life he claims he wanted.

The Problems With "That Damn Donna Reed" Are Why I Never Rewatch It

The Gilmore Girls Episode Completely Undermines Rory

Most of the Gilmore Girls fandom is in agreement that season 1 Rory is the best Rory, and it's scenes like her arguing with Dean about the Donna Reed image that prove as much. But the way "That Damn Donna Reed" makes Rory the heroine of the episode only to turn her into the butt of the joke makes it a hard in my rewatches.

Lorelai grew up with and ran away from an unrealistic set of expectations, so there's a lot of wisdom she could have imparted on Rory.

Not only does Rory fail to make her point to Dean and completely back down, but Lorelai turns her into a laughingstock. It feels like a huge missed opportunity to have Lorelai poke fun at Rory rather than have a serious conversation about why her daughter is dressed that way. Lorelai grew up with and ran away from an unrealistic set of expectations, so there's a lot of wisdom she could have imparted on Rory here. To cap it all off, the Gilmore Girls episode ends with Christopher, so you can see why it's not high on my list