Gilmore Girls: 20 Things That Make No Sense About Rory's Relationships

Alexis Bledel as Rory Gilmore in Gilmore Girls

When it comes to Gilmore Girls, people have a lot of opinions. This is especially true with regards to Rory Gilmore’s romantic relationships. One of the most polarizing debates in TV history is over which guy the young Gilmore should have ended up with. We see fans of the show falling into three main camps: Team Dean, Team Jess, and Team Logan. Rory had her fair share of happy moments and disasters with all three, and if you were an avid viewer of the series, you’ll undoubtedly have your own opinions on this crucial matter.

While the arguments for and against these three men in Rory’s life could go on ad nauseam, one thing we can all agree on is the fact that there were a lot of confusing moments when it came to Rory’s relationships over the course of the show. People have pointed out a number of perplexing things about Gilmore Girls as a whole, like the fact that the Gilmores eat nothing but junk food but remain looking healthy, that their caffeine consumption is really very worrying, and that everyone in Stars Hollow is obsessed with Rory for some reason, but it’s actually the relationships Rory has that pose the biggest, most confusing questions. From her affairs with married men to her inability to break up with people, Rory Gilmore has a lot to own up to-- both in the original Gilmore Girls and the Netflix revival, A Year in the Life.

With this in mind, here are 20 Things That Make No Sense About Rory’s Relationships.

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Alexis Bledel as Rory and Jared Padalecki as Dean in Gilmore Girls
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20 Kept dating Dean when she was in love with Jess

Alexis Bledel as Rory and Jared Padalecki as Dean in Gilmore Girls

Early on in the show's run, the were two definite camps: Team Dean and Team Jess. A lot can be said, both positively and negatively, of these two suitors, but one thing that can’t be disputed is the fact that Rory messed up big time in the way she handled her feelings. Instead of just coming clean to Dean about her new feelings for Jess, she strung the poor, tall sap along while she not so discreetly yearned for bad boy Jess.

Her flaky refusal to own up to her feelings and be truthful to her high-school sweetheart-- and herself-- makes absolutely no sense.

This was one of the more baffling relationship developments that happened in the early days of Gilmore Girls.

19 Her affair with Dean when he was married

Alexis Bledel as Rory and Jared Padalecki as Dean in Gilmore Girls

As if it weren’t bad enough that Rory let Dean believe she was still in love with him while harboring feelings for Jess, she took a plunge deeper into the dark side when she suddenly decided she wanted him back - after he had gotten married. Dean had already moved on and tied the knot with Lindsay, but for some reason Rory decided there weren’t enough guys at Yale and she just had to get back with her ex-boyfriend.

Instead of respecting Dean’s marriage and respecting his choice to move on from his past with her, Rory embarked on an affair with her first boyfriend, thus throwing this poor guy’s life into chaos. That’s not to say he’s not to blame too, because as we all know, it takes two to tango. 

18  Getting upset with Logan while they’re on a break

Matt Czuchry as Logan in Gilmore Girls

While it might be understandable that Rory got upset with Logan for sleeping with other people while they were on a break, it’s her double standard behavior that’s really the confusing part of this whole plotline. While she may have thought they were just taking some time apart from each other, and Logan was under the impression they had broken up for good, the fact of the matter is, Rory is getting upset with her ex for seeing other people.

Isn’t this coming from the girl who led her boyfriend on while she was secretly in love with someone else?

Isn’t this the same Rory who slept with her married ex? Rory’s shortsightedness of her own romantic misdeeds is utterly confounding, especially when she decides to get upset with Logan for fooling around with other people when they weren’t even together anymore.

17 Most of her relationship with Jess involved Dean

Alexis Bledel as Rory and Milo Ventimilglia as Jess in Gilmore Girls

When Rory finally ended up with Jess after her breakup with Dean, many were overjoyed by this long-overdue coupling. To finally see Rory with someone who matched her intellectually after her time with the sweet but dim Dean was a great relief to many viewers, and everyone was undoubtedly excited to see where this new relationship would go.

Well, unfortunately, Rory and Jess’ relationship seemed perpetually shadowed by the ghost of her relationship past. While we should have been watching her romantic storyline with Jess blossom, we somehow ended up with Dean constantly popping up in their narrative. To build up all this tension between Rory and Jess, to have her go through a break-up with Dean, and then to have this end with them being constantly bothered by Dean’s presence throughout their relationship? It’s hard to understand why this happened.

16 Telling Jess to “Not Say A Word” After They Kiss

Alexis Bledel as Rory and Milo Ventimilglia as Jess in Gilmore Girls

Rory and Jess share their first kiss at Sookie and Jackson’s wedding. While this might have been a hit for people rooting for Rory and the bad boy to get together, it doesn’t take away from the fact that this first kiss happened while Rory and Dean were still together.

Rory’s complete disregard for monogamy isn’t the only thing that’s confusing.

What’s more perplexing is the fact that she tells Jess “not to say a word” after the smooch occurs. You’d think that after just cheating on your boyfriend with the person you’ve been dreaming of being with for so long, you’d want to have a conversation to sort things out. Like, “where do we go from here?”, for instance. Or, “let’s talk about how I need to break up with my boyfriend so we can be together.” Nope, instead she insists Jess shuts up and she flees from the scene.

15 She dates someone from the privileged world she hates

Alexis Bledel as Rory and Matt Czuchry as Logan in Gilmore Girls

Many people who have revisited Gilmore Girls as adults have criticized Rory for her complete lack of self-awareness as a privileged, white woman. People who may have been fans of the show as young teens now often view Rory as a bratty, spoiled girl who doesn’t realize how good she’s got it, and this has led many people to lash out against both her and Lorelai.

While her inability to realize she’s privileged is confusing in itself, what’s also confounding is the fact that she decides to date Logan, who is from the upper class world she professes to hate. Constantly pretending that she’s not like her privileged Yale pals, Rory assumes a lifestyle with Logan that is exactly like the one her mother tried to steer her away from. The fact that she dates Logan, and takes so long to realize she’s in this world, is just bizarre.

14 She complains when Logan’s fiancee moves in with him

Alexis Bledel as Rory and Matt Czuchry as Logan in Gilmore Girls

Rory commits a whole heap of relationship crimes, including cheating on several of her partners as well as having double standards and being flaky, but it’s the way she reacts to the news about Logan’s fiancee moving in with him that really makes you want to question everything.

In the Gilmore Girls revival, we learn that Rory and Logan have been having an affair, despite the fact that Logan is getting married to someone else. While Rory seems totally fine with the adultery, the thing that really grinds her gears is Logan’s announcement that his fiancee is planning on moving in with him. Living with your fiance is a completely normal thing to do, yet Rory gets upset when she finds out this is happening. 

13 She repeatedly ignores Logan’s bad habits

Alexis Bledel as Rory and Matt Czuchry as Logan in Gilmore Girls

Love him or hate him, we can all agree that Logan knows how to have a good time-- maybe too much of a good time. In fact, it’s a wonder that Rory stayed with him for so long when all he did was party like his life depended on it.

In several episodes we see Logan getting so trashed that Rory has to practically carry him out of the bar.

Not only that, but it seems like his drinking often led to some pretty bad temper tantrums on his part. Remember the awful sit-down with Jess, Rory, and Logan? Fueled by drink, Logan proceeded to verbally attack Jess and then Rory in turn. Of course, it’s this row that led to Logan and Rory’s split, but even after they got back together, Rory still put up with a lot of nonsense from Logan that she definitely should not have taken from him.

12 Putting her boyfriends before her dreams

Alexis Bledel as Rory and Lauren Graham as Lorelai in Gilmore Girls

Some of the first impressions we’re given of Rory at the start of the show are that she’s smart, hard-working, and she aspires to be a journalist. Why is it that at the slightest sign of romance or boy-trouble, Rory is ready to throw in the towel on her dreams?

First it was her love for Dean that made her want to give up on going to Chilton, then it was Logan’s dad who told her she wasn’t good enough to be a journalist that made her drop out of Yale. She then gets so distracted and caught up in Logan’s world of parties and privilege that she completely neglects her education and the pursuit of her writing dreams. For someone who was made out to be so focused at the start, it’s very confusing that she’s so willing to drop everything for the men that come swanning into her life.

11 Pretending to be interested in Robert

Rory is guilty of doing some pretty sneaky things on Gilmore Girls, and most of the time it doesn't make sense why she’s doing them. She clearly has no qualms about stringing people along, as we’ve seen with Dean, and she took this one step further by pretending to be interested in a guy for the singular reason of making someone else jealous. 

Surely she didn’t need to string poor Robert along for that.

While the old “make someone jealous by hanging out with someone else” trick is one of the oldest in the book, Rory’s date with the seemingly nice Robert at Finn’s Tarantino party is pretty confusing. Sure, she clearly wanted to make Logan jealous, but they immediately make out behind Robert’s back at the party and confess they liked each other anyway. 

10 She hid her friendship with Dean from Jess

Jared Padalecki as Dean Forester and Alexis Bledel as Rory Gilmore and Milo Ventimiglia as Jess Mariano in Gilmore Girls

When Rory embarked on her relationship with Jess, there was hope for a new beginning without the stress of her past with Dean. Rory finally got to be with the guy she really wanted, and we all thought that would be good enough for her.

Well, her decision to stay friends with Dean certainly through a spanner in the Jess-Rory works. For some reason, Rory thought it would be a great idea to hide the fact that she was still hanging out with Dean from Jess, because obviously sitting on a bed of lies is a great way to maintain a relationship. That she didn’t come clean to Jess about this friendship is confusing to say the least, and by keeping it a secret, she only made Jess suspect there was something more going on.

9 She goes from commitment-phobe to commitment-keen

Alexis Bledel as Rory and Matt Czuchry as Logan in Gilmore Girls

Another confusing character arc we see is Rory's sudden change of heart about the whole concept of relationships. Rory and Dean’s first breakup in season 1 is triggered by the fact that she doesn’t say “I love you” back to him.

This leads us to believe that the whole idea of big romance really isn’t Rory’s thing.

Then with Logan, she acts as if she’s fine with a casual relationship, but reacts badly when she finds out he’s dating other girls. We see her going from commitment shy with Dean, to commitment-keen with Logan, making things pretty confusing when it comes to figuring out what it is that Rory really wants. To make things even less straightforward, when Logan finally pops the big question in season 7, Rory turns him down. Clearly Rory is all over the place, like many of us are when we’re growing up, but that doesn’t make things any less confusing for us viewers.

8 She dates someone who is just like her father

Alexis Bledel as Rory, Matt Czuchry as Logan and David Sutcliffe as Christopher in Gilmore Girls

Entertainment Weekly revealed that Logan was actually modeled after Rory’s dad Christopher. In the article we learn that Gilmore Girls creator Amy Sherman-Palladino knowingly made Logan similar to Christopher in order to highlight Rory’s father issues. She says: “We wanted Rory to date her father. Every girl has a father issue, and Logan was Christopher. Logan was charming, smart, and not quite the dependable soul that you need. Or, at that time, was not the great dependable soul.”

It’s still strange that Rory chose someone with so many of the qualities that she found disappointing in her dad, and that this relationship was the longest one of all. Christopher was not good news for Lorelai, and in the end, neither was Logan for Rory. Why she stayed with someone who exhibited such toxic behaviors is something that will continue to confuse us.

7 She sets aside her own views for Dean’s

Alexis Bledel as Rory and Jared Padalecki as Dean in Gilmore Girls

In the infamous “Donna Reed” episode in season 1, we witnessed just how easily swayed Rory could be when it came to men. In it, Dean reveals his traditionalist views on family life and his admiration of the 1950s-style nuclear family seen in The Donna Reed Show. Rory and Lorelei berate him for his conventional views, and Rory ends up getting upset over his fantasies of women as housewives. However, in order to please Dean, Rory invites him over for dinner, in full Donna Reed garb, and pretends to be a good little housewife cooking for him.

The whole thing is very confusing in light of Rory’s views about women’s independence, and also contradicts the ideals she been raised on by Lorelai.

Clearly Rory’s need to please her boyfriend trumped her commitment to her own beliefs, and the whole episode leaves a rather sour aftertaste.

6 She doesn’t seem bothered when Logan doesn't say "I Love You" back

Alexis Bledel as Rory and Matt Czuchry as Logan in Gilmore Girls

Inseason 1, Rory’s failure to say “I love you” back to Dean when he confessed his deep feelings for her resulted in their first break-up. Dean was heartbroken, and who could blame him? Rory shouldn’t have felt forced to confess feelings she didn’t really have, but at the same time, that kind of rejection is crushing.

When Rory told Logan that she loved him and he didn’t reply, she acted totally cool with it, since she had gone through a similar experience with Dean. However, as fine as she seemed about the whole thing, it’s pretty perplexing that she wasn’t more shaken by his lack of response. Anybody else in that situation would feel pretty vulnerable and rejected, so her lack of reaction when she knew how upset it had made Dean previously is kind of confusing.

5 Tristan just disappeared

Alexis Bledel as Rory and Chad Michael Murray as Tristan in Gilmore Girls

Ah, Tristan. The one that went away too soon. Rory’s short-lived fling with the gorgeous Chilton bad boy was a blip on the radar compared to her other relationships, but it’s one that certainly had effects on her chemistry with Dean. Tristan and Rory shared some pretty flirtatious moments, and of course there was their kiss. Although Rory was both put off and attracted to Tristan in equal measure, there’s no denying that she definitely had some feelings for him.

When Tristan announced out of the blue that he was being sent away to military school, it didn't seem natural for the story at all.

It likely had more to do with actor Chad Michael Murray getting his role on Dawson's Creek than there being any indication that his storyline on Gilmore Girls was done. It seemed like his arc with Rory had just begun.

4 Her affair with Logan

Alexis Bledel as Rory and Matt Czuchry as Logan in Gilmore Girls

We learn from the Gilmore Girls revival that Rory has been secretly having an affair with Logan in London, despite the fact that he’s engaged to someone else. There are many people who were undoubtedly overjoyed to see Logan and Rory back together again, but the fact that he’s in a long-term relationship with someone else certainly doesn’t paint either one of them in a good light.

The confusing thing is, Rory already turned down Logan when he proposed to her in season 7. Why did she decide to rekindle their love, especially knowing he’s promised to someone else? Her behavior here is certainly baffling, but for anyone still firmly in the Team Logan camp, are you sure you want to back a cheater?

3 Her brief visit to Jess in Philadelphia

Alexis Bledel as Rory and Milo Ventimiglia as Jess in Gilmore Girls

Any fan of Jess will agree that Rory’s impromptu trip to Philadelphia to visit him while she was upset with Logan was definitely confusing. She basically led Jess on, making him believe that her visit meant something more than just a distraction from her current relationship problems. Rory was still upset with Logan for getting with various girls during their separation, and she was essentially using Jess as a means of getting back at him. Jess clearly didn’t realize this and kissed Rory, only to be pushed away by her and told that she was still in love with Logan.

Not only did this scene paint Rory in a negative light, it was also confusing to see her use someone she cared about in such a manipulative way.

Most of us would have thought she'd have more respect for Jess, but clearly there’s no end to Rory’s mistakes when it comes to her time spent with Logan.

2 Her awkward treatment of Marty

Alexis Bledel as Rory and Wayne Wilcox as Marty in Gilmore Girls

For most of the show, Rory is painted out to be a sweet, caring person. However, looking at some of her friendships and relationships, you’ll see that Rory wasn’t always the most considerate pal. One of the most painful relationships to watch in the show was that of Rory and Marty, her friend from Yale.

From the first moment Marty was introduced, we could see that he clearly had a thing for Rory. The more they hung out, the more you could see how much he wanted to date her. Of course, Rory didn't need to date Marty if she didn’t want to, but every time she and Logan were with Marty, she never really had his back. She didn’t do much to save Marty from being humiliated by the privileged Yale set, and always took Logan’s side over her supposed friend’s.

1 Stringing Paul along for years

Alexis Bledel as Rory and Bryce Johnson as Paul in Gilmore Girls

Without a doubt, the most savage and confusing of all Rory’s relationship is the one she had with Paul. Introduced to us in the revival episodes, Paul had apparently been dating Rory for two years when we first meet him. Of course, Rory was sleeping with Logan while being Paul’s girlfriend, and instead of just breaking up with him, she kept putting it off. 

She kept forgetting that Paul even existed!

How does someone forget they’re in a relationship? Seeing Rory right down “Break up with P” on a post-it note instead of just giving him the courtesy of a phone call or a visit is quite simply baffling.


What else doesn't make sense about Rory's relationships on Gilmore Girls? Let us know in the comments!

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