What We Can Learn From Rory Gilmore On How Not To Date

My love for Gilmore Girls runs deep. Every fall when the air gets crisp and the AC gets turned off, I become giddy knowing it’s almost time to settle in and begin another top-to-bottom round of my comfort show. I’ve watched the series from beginning to end more times than I can count – although my commitment sometimes fizzles out after season six (iykyk). 

But my love for the show doesn’t mean I can’t acknowledge that both Rory and Lorelai have their flaws – and let’s be honest, some glaring ones, at that. These downfalls are especially obvious when it comes to the Gilmore girls’ love lives. It’s no secret that Lorelai doesn’t have the best track record when it comes to men, a trait she appears to have passed on to her daughter. 

Every Gilmore Girls fan has their favorite Rory boyfriend, but one thing we can all agree on? She treated each of them pretty terribly more often than they deserved. Read on to see Rory’s biggest dating faux pas. 

Warning: Spoilers ahead! 

Don’t Sleep with Married Men

I had to start with the most obvious one. When Rory and Dean – who was very much married – got together in the season four finale, I don’t think I’m alone when I say my heart sank. At this point in the series, viewers knew that Rory had the tendency to be self-centered, but her behavior with Dean took it to the next level. She did, after all, refer to him as “her Dean,” not as “Lindsey’s husband Dean” like he was at the time. Oof. 

It seems like Rory’s hookup with Dean was the beginning of a selfish streak for her. From then on, impulsive, irrational behavior became her MO. (For more details, see the entirety of season six.)

Don’t Thank a Guy When He Kisses You

Sure, Rory’s “thank you” response after Dean kisses her for the first time is a fan favorite. But can we have a moment of silence for poor Dean’s masculinity? 

In a way, we can forgive Rory’s awkward response because in her high school years she was, well, awkward. Not to mention, Dean’s impromptu kiss caught Rory off-guard. But there are so many ways that first kiss could have gone better. And the way she bolted out of the store (with the corn starch, oops!) made it that much worse. She didn’t have to kiss him back, but give the guy something to work with – a smile, a flirtatious wink, anything!

Don’t Play Games

We all knew that Rory and Jess would end up dating from their very first interaction. A swoon-worthy, mysterious guy who’s also surprisingly well-read? One can hardly blame Rory for falling for him. But she didn’t have to play with Dean’s heart the way she did. 

The way Rory used her relationship with Dean to make Jess jealous was one big eye roll. For the most part, Dean was a good boyfriend to Rory. He put up with her strenuous school schedule and supported her dreams, even if his priorities didn’t align with hers. 

Rory probably didn’t mean to be malicious or hurt Dean in any way, but at the end of the day, her plan worked. Dean broke off the relationship, and she and Jess officially started dating, just like she (subconsciously?) intended. But that’s no way to start off a new relationship. The lesson: Make your feelings clear to your man and don’t use him as a pawn to get what you want. 

Don’t Hook Up with a Wookiee 

Or any stranger, for that matter. 

The Gilmore Girls four episode revival A Year in the Life left a lot to be desired, but few plot points had fans scratching their heads more than Rory’s rendezvous with a stranger dressed as a Star Wars character. Hooking up with someone she just met was out of character for Rory, and she might have to face the long-term consequences from it (fast forward to the last four words of the revival for more explanation). Let’s learn from Rory’s mistakes and all agree that sleeping with strange men (Wookiee or otherwise) doesn’t bode well for anyone involved.

Don’t Forget Details About Your Man (Like His Name)

Speaking of A Year in the Life, let’s take a moment to remember Paul – because Rory sure didn’t. 

Paul was Rory’s boyfriend (if you could call him that) who she was always forgetting throughout the show’s revival. She forgot when they had plans, forgot details about him, and even forgot his name. 

Just like Rory, we don't know much about poor Paul. But we know he deserved more respect than Rory ever gave him. And the thing is, he seemed like a genuine, unproblematic guy – which might explain why Rory wasn’t into him. 

Don’t Lead Guys On

Remember Marty, Rory’s deadpan and charmingly awkward friend at Yale? It was clear that he had feelings for Rory, but she was either completely oblivious or didn’t mind making him believe he stood a chance with her. Rory led Marty on from the very first time they met during their uncomfortable late-night interaction in the dormitory hallway until she hung him out to dry as soon as she bagged Logan. And who can forget the awkward dinner situation with Marty and Logan’s lavish friends? Talk about emasculating.  

In the end, Marty and Rory probably didn’t have the chemistry to go the distance, but she should have made that clear from the beginning, or at least once she started developing feelings for Logan. 

Don’t Give Up on Your Relationship

Ready for a hot take? Rory should’ve accepted Logan’s marriage proposal – or at least fought a little harder to stay together. 

The reason Rory turned Logan down was because she didn’t want to move to San Francisco, desiring to start her career instead. I’ll admit that Logan’s ultimatum – “marry me and move to the other side of the country, or we’re breaking up”– wasn’t fair, but Rory could have tried harder to keep the relationship afloat. There are plenty of journalism opportunities in San Francisco, and she had no shortage of connections through Logan’s family. It’s true that Rory wasn’t on the best terms with the Huntzbergers at the time, but it’s reasonable to assume that a family so focused on status and image would help their soon-to-be daughter-in-law land a job – and a good one, at that. 

Rory and Logan’s relationship was going well after some shaky ups and downs, and she could have easily started a new career out in California if the two had stayed together. If Rory wasn’t ready for marriage, she could have at least suggested they discuss the matter further rather than turn him down outright. 

Closing Thoughts 

After all these years of watching her trials and triumphs from my couch, Rory has become like a family member – I can critique her behavior all day long, but if a GG novice badmouths her, all of a sudden I’m at bat for Rory Gilmore’s character. 

Personal connections aside, it’s clear that the youngest Gilmore girl needed some lessons in the dating department. Let’s all learn from Rory’s mistakes and aim for relationships that are healthy, respectful, and unproblematic. 

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