You can’t smell snow in the air just yet, but it is definitely that time of year where the itch to rewatch Gilmore Girls for the millionth time comes around again. It’s a show that makes you laugh, cry, throw things, all while feeling so incredibly cozy and happy. It’s one of a few shows I happily watch over and over, and each time it feels like the first time.
There’s so much we can unpack from this comfort show, but one of the biggest debates I usually see is Rory Gilmore’s (played by Alexis Bledel) dating history. Who’s the best, the worst, the cutest, etc., etc…
Which is exactly what we are going to unpack today!
We’re going to go over each of Rory’s love interests and discuss the themes of these men, why they were important, and how we tend to see these sort of men in our own love lives.
Does everyone have their cup of coffee or wide assortment of disgustingly sugary snacks? Great, let’s go.
ATTENTION: THERE WILL BE SPOILERS AND I DO NOT OWN THE RIGHTS TO ANY PHOTOS, I GOT THEM FROM THE INTERNET OBVIOUSLY
Dean Forester (played by Jared Padalecki)
Oh Dreamy Dean. We’ve all had a Dean in our lives because Dean is the first love. The first almost adult love, the first kiss, the first of many things for Rory. Dean is depicted as a fun, edgy-but-not-as-smart-as-Rory, “new kid” with beautiful eyes and oh-so-touchable-hair, he’s a bit of a precious heartthrob. He’s the guy that comes into town and has everyone’s attention, but he only has eyes for Rory.
That makes us fall in love with him immediately. I remember rooting for Rory and Dean many times, because they just seem so cute together when they’re relationship is introduced. Afterall, they have many cute moments and at first their innocence is adorable.
But we also have to remember that Dean is the first boy Rory hid from her mom, Lorelai (played by Lauren Graham). That was the first of many mistakes Rory made when it came to Dean.
We know that Lorelai and Rory have a very blurred lines relationship. Being so close in age, their bond runs strong and deep, with moments that show their relationship off as best friends who happen to be mother and daughter. When Rory is dishonest about her budding relationship with Dean, this sets a small rift between her and her mother, who is desperate for Rory to not repeat her own life choices.
However Dean doesn’t stay in everyone’s good graces for long. He is the perfect archetype of an insecure young man. His insecurities show through in his behaviors, such as being threatened by any other guy giving Rory attention, stating his dominance whenever the opportunity arises (sometimes getting in fights over it) and in some moments can be seen as quite controlling and clingy.
Eventually, Dean breaks up with Rory because she wasn’t ready to verbalize back that she loved him, showing impatience and selfishness. Not to mention it was a very public breakup at the all night Dance-A-Thon which is just plain embarrassing for all parties involved.
Everyone’s relationships are on different timelines, and we can certainly understand where Rory gets her anxious yet avoidant attachment from, but Dean only gets worse.
He desperately tries to cling onto the fact that he is Rory’s first love, with the wholesome, small-town boy act, but Dean has very little regard for people other than himself, which is seen when he cheats on his later season wife with Rory, causing a huge disturbance to everyone’s life and shattering his marriage.
Not to mention Dean and Rory had very different ideas for their future. Rory was ambitious and wildly intelligent, hoping to go to Harvard someday, where Dean did not show an effort to ever leave Stars Hallow or a desire to achieve any other stereotypically ambitious goals.
The first love is usually a love we grow out of, and remember it as a special time in our lives, regardless of the outcome. Rory outgrew Dean, rather quickly might I add, but they both had a hard time truly letting the other go, as seen through their later affair. Their realtionship became a chore for them both, with Dean losing interest in Rory’s bids for attention and more or less slow fading himself out of the realtionship, both knowing they weren’t on the same level anymore but not having the life experience to know what to do in that setting.
First loves can be great for a lot of reasons, they spark our desires and intrigue. They show us how quickly we can grow and change, or how much we have yet to grow. They help us refine what we are looking for in life and make sure that we are never, ever, the same again.
Rory’s relationship with Dean had many consequences. It strained relationships, caused a town-wide scandal, and I think had a lot of negative effects on Rory as well.
Rory was already struggling to come out of her shell, having difficulty with connecting with peers at school, or maintaining relationships with friends like Laine from Stars Hollow. She was also just starting to truly get to know her grandparents and the lifestyle they are accustomed to, being a complete 180 from the life she has always known. Understanding that her mother and father never stayed together, and her mother’s example of being wildly avoidant to happiness and love romantically, without a doubt left a heavy impression on Rory.
I think that Rory was just as impacted by her relationship with Dean. Although empowering in some ways, it gave her more reason to pause, and just as much reason to feel a bit nervous and unsure with herself. Wondering if she was broken in some way or was wrong for not being ready on Dean’s timeline.
The thing is, as young girls, we were never taught that our own timeline was ok! We were taught to cater our near entire existence to the convenience of men, and usually our first (or second…or third…) loves can act as a wakeup call to those behaviors we were raised with.
First love’s are impactful no matter how long the relationship lasts, and Dean certainly makes an impression with Rory, her mom, and the rest of Stars Hollow. Let’s see if she learned her lesson, shall we? Spoiler, she never does…
Tristan Dugray (played by Chad Michael Murray)
Ok listen to me here, I LOVE Chad Michael Murray, he has a very special place in each of our hearts, but we must put that opinion aside and focus on Tristan here, got it?
Tristan, Tristan, Tristan…you sexy bastard. He is so appealing and repulsive at the same time. Tristan is the bad-boy of the school, the hot-shot, the biggest catch. He’s probably been with everyone in school, but also everyone wants him so I guess that works out pretty good for him.
Tristan is the bad intentions kinda guy. The one who very clearly doesn’t respect boundaries, even ones as simple as calling Rory by her real name, or pushing boundaries with her knowing she is seeing someone. He is a boy masquerading as a man and is the type that would make things overly sexual far too soon, and is generally a pest towards Rory thanks to his immaturity. He tends to get upset when not given his way, and always acts arrogant towards those around him.
Did I mention he comes from a rich family and is so darn charming? Rory and Tristan have great banter together, we can hardly blame Rory for falling for his ruse. When I was 16, I wouldn’t have seen his red flags either!
The thing with guys like Tristan is they usually have the potential to be really incredible guys, with amazing opportunities ahead of them, but act quite entitled for the things they want in life because they are always trying to get their emotionally unavailable parents attention. They are incredibly attractive and annoyingly smart, but use that intelligence towards manipulation. When their attention is on us we feel special, no matter how much we try to fight it.
They didn’t really have the abundance of cute moments we hoped for, and in truth their time was cut short when he was sent away to military school. I think this relationship could have had a really nice arch if given the right timing, but their cat and mouse game probably played itself out too soon and people got bored with it so they wrote him out.
To our surprise, Tristan was in “Gilmore Girls: A Year in the Life” at a Chilton reunion/event, despite never actually having graduated from Chilton (because he went away to military school, remember?), and to our deepest regrets was played by another actor. No hate to that guy, but we all would’ve rather he not been written in at all than played by someone other than CMM.
Regardless, Tristan is the first fun and dangerous lover of Rory, who initially wants absolutely nothing to do with him. He further causes her some mental harm with his constant pushing of boundaries and subtle manipulation. He’s a guy that should really do some soul searching on his own, but often goes through the ladies like Kleenex.
He’s the guy we all should stay very far away from, but often don’t.
Sometimes, if we are really unfortunate, our Tristan is our Dean. The bad boy we fall in love with for the first time. There can be a lot of benefit to coming across men like this in the wild. Like learning what our boundaries are and how we want to enforce them in our lives. Learning what we feel comfortable with physically and what we don’t.
But mostly, they’re just fun to look at and occasionally banter with.
Marty (played by Wayne Wilcox)
Everyone forgets about Marty. No offence but it’s easily done when he is arguably the most normal guy Rory almost dates!
Marty is one of the guys Rory befriends while at Yale (oh yeah, spoiler she doesn’t go to Harvard), and is an unassuming guy that treats everybody nicely. He sees Rory as someone who is not just a friend, but a real human being with a dynamic personality and oh I don’t know, emotions and feelings, and they generally have a good time together.
Marty is much more down-to-earth than Rory’s previous male encounters, as he also is someone that has to work hard to earn his place at Yale, giving them common ground with each other.
He’s the kind of guy that is eternally in the friendzone, despite our therapists silent urge for him to be released. Logan, who we will talk about soon, was a bit of a cockblock for Marty, but in general he is a fairly unproblematic guy, aside from a small moment in the final season that isn’t really worth mentioning. I think because of his “normalcy,” Rory isn’t fully attracted to him and without the cat and mouse game that she’s used to, she turns to more exciting dynamics to fulfill that toxic urge.
Due to Marty having a very short time on the show, we don’t have much to discuss with him, but I supposed for discussion’s sake we can call him the nice guy.
The nice guys are the ones that treat us with respect, and might not necessarily go above and beyond for us (though some certainly do), but are more or less smart choices when it comes to romantic partners. They’re the guys that probably should be our first loves, so that we can learn healthier ways to connect with others, especially our romantic interests.
I don’t think we’ll ever fully understand why the toxic, yet thrilling, behaviors of “bad boys” will peak people’s interest at young ages, though we certainly theorize plenty. That’s probably a discussion on the patriarchy and our modern society that we can save for another day.
Unfortunately for Marty, he was boring and we much prefer Rory’s other, more chaotic and stupidly handsome romantic interests to entertain us.
Logan Huntzberger (played by Matt Czuchry)
Honestly, I keep sighing each time we make it to a new boyfriend, because we love them, and we hate them, we love to hate them, but we sure do love to love them.
Logan Huntzberger is who Tristan probably would’ve been in college had he not gone to military school. Or maybe he did become this, who knows.
Logan too was a spoiled and entitled rich kid. He is a stereotypical playboy who acted with reckless abandon, consequences for others be damned (because mom and dad would always clean it up). We honestly are not sure what his motivations in life were beyond having fun before going into the life his parents had planned for him. From “Gilmore Girls: A Year in the Life,” we know that Mr. Huntzberger leads a successful life, carrying on many of his college like qualities, but I’m getting ahead of myself here.
The Gilmore Girls community is back and forth on their opinion of Logan. On one hand, Logan does a great job of helping Rory break out of her shell and embrace some of the fun in life that she deserves. Rory is also a good influence on Logan. She teaches him the things in life that he needs to take more seriously, opening his eye to the ways that people like her live, and she just might very well be a part of his success later on in life because of that perspective.
Logan is Rory’s primary love interest through the entirety of college, and even holds an important role in the continued limited series.
The thing with guys like Logan, are they have the same appeal as those like Tristan. They are charismatic, smart, fun. They also have all the negatives. They can be hot and cold, uncommittable, dishonest and disloyal. They bring you in, you think you can change them, and maybe they try to let you, but they almost always stay exactly the same because that’s what benefits them the most.
Rory and Logan’s relationship started casually, and when Rory reveals to him that she will never be a casual girl, he surprises us by saying he’ll be a more serious guy, all because he doesn’t want to lose her. That’s cute when we first think of it, but with time we see how this dynamic plays out and how their relationship continues to have an up and down nature.
Do we remember that lifestyle Rory’s grandparents had that was completely different from hers? Well Logan lives that same lifestyle, and comes from a very rich, very prestigious family that always, and I mean always, has a plan for their children, whether they agree with it or not.
One of the biggest struggles in Rory and Logan’s relationship was the difference in upbringing, and therefore a difference in opinion on how to live, period. Logan would never be prepared to leave that lifestyle despite his love for Rory, and this brought a huge rift between them because Rory didn’t have the same entitlement as Logan.
In all truth, this relationship might have been a bit of a downfall for Rory. Mitchum, Logan’s father, is a big name in the journalism industry, which Rory desperately wants to be a part of, mentioning it even as early as season one. He tells Rory that he doesn’t believe that she is cut out for journalism, and in turn crushes her very soul, leading her to feel hopeless and directionless in life, leading to her dropping out of Yale. Which to our shock, Logan didn’t do much to help the situation, of her dropping out of school or with the relationship with his father.
Commentary of Rory’s character is a whole different blog post, but long story short, this wake up call gives Rory a reason to pick herself up again…sort of…eventually? She rebuilds her life based on her recent choices, and sees that Logan isn’t going to ever be the person she wants or needs him to be. Rory gives herself a pretty serious pitty party, reinviting many insecurities to the mix that she might have delt with, and her life veers off on another path.
Many believe that Rory and Logan would never have had the momentum or stamina to maintain a healthy, committed relationship, and I am inclined to agree, but we see both characters in a different light in the limited series later on.
At that point, I was really sick of Rory, her life choices, and romantic partners. Sure the drama is great for the show, but come on. Even the stupidest people can wise up eventually. Especially with her consistent friendship with Paris (we love Paris here), you’d think she’d have more people in her life to have given her a wake up call earlier, or pushed her a little harder…or at the very least have suggested a good therapist!
Logan is the type of guy that was the fun hookup that we just kept hooking up with and hoped would love us enough to change, knowing deep down it probably wasn’t going to last. Since we didn’t learn our lessons from the Dean’s or Tristan’s, we have to learn them from Logan’s. Which is arguably something that has the potential to be far, far worse.
Something about college makes young women really believe that we can change a man, or rather that the love we hope they feel for us will change them. Again a conversation on society for another day.
That love is almost entirely in their pants, and without a fully functioning frontal lobe (or sometimes even after), we simply can’t trust them to be who we want or need. There isn’t enough take-out Chinese and pizza or Paris Geller level interventions in the world to heal those wounds, though we try, everyday.
The college guy is just as impactful as the first love. Usually he is our first adult love, where we have different perspectives on life than we did at 16, might be more emotionally and sexually experienced, and we believe that the world is our oyster.
Like our first love, it completely changes us, and teaches us even further who we are, what we want out of life, and who we want to experience it with.
Having a Logan in your romantic experience is important, though if you can learn the lessons through others and skip over him entirely to find Prince Charming, that is ideal (though unrealistic).
As I said, we love Logan, we hate Logan, we love to hate Logan…and we love to love Logan.
Jess Mariano (Milo Ventimiglia)
*Brief trigger warning for mention of sexual assault*
Jess…oh Jess…oh Jess…perhaps maybe the favorite of them all?
Jess in so many ways fits right in with Rory’s intellect, wit, and mental stamina. They bond deeply over literature of a wide range of styles, push each other to be better in life, and it seems to be the first truly deep connection they’ve both experienced.
Yet, Jess is a very troubled person. He purposely does poorly in school, consistenly acts out and is a bit of a terror for the town, his uncle Luke especially. He has a challenging dynamic with his mother, who is absent throughout most of his life, and his first real experience with discipline and concequences comes from his time living with his uncle.
This leaves Jess as someone to consistenly unreliable emotionally. He often doesn’t have the capacity to support Rory emotionally, and in one instance acts completely different than we would have expected him to up to this point.
Let me be perfectly clear. Sexual abuse, or abuse of any kind is unexcusable. If you know the context of the episode, Jess was most definitely acting out here. Rory had revolked her consent while making out and at first he did not listen, then he exploded, which also led to a heated moment between him and Dean. Again, not excusable, and showed Jess wasn’t ready to be a boyfriend to anyone yet. There was never a moment like this before for the pair, and there wasn’t another one after.
In short, Jess lives a complicated life, but he was always the one pushing Rory to do more with her life, to not listen to the rich bastards that try to discourage her, and to take life head on, leading a bit by example.
Jess was unfortunately flighty as well. Stars Hollow felt like a cage for him, where he was the main attraction to gawk and point at. He leaves without notice, breaking Rory and Luke’s hearts in the process. For all of Jess’s charm and connection with Rory, we were always left wanting more for him, and for Rory too.
That wasn’t the end for Jess though. We see him throughout later seasons, and by the end of the show he is a completely different man. The man we always wanted him to be for Rory. He is a successful author, having written a book, and continues to push Rory by challenging her life choices, namely that of her relationship with Logan.
We can tell that these two always wanted the best for each other, and they wanted the best thing for the other person to include each other. Rory did a lot to bring out the good qualities in Jess, and he did a lot to shape her viewpoint on her own life, their influence on each other was always back and forth, but their timing was always off with each other.
A timing we regret never made right, though with Luke and Lorelai eventually (finally) getting together, we aren’t sure how that dynamic would work anyways. For viewers, I think it was more important that Luke and Lorelai got together than Rory and Jess, since Logan was still around.
I can speak for most Gilmore Girl fans, that we really, REALLY, hope that Jess and Rory’s timing becomes right someday, even if we never get to see it happen.
The right guy, wrong time trope is a hard one to experience. Some say that if it was the wrong time, it was definitely the wrong person, but I don’t always follow that logic so strictly.
I wholeheartedly believe that people come into our lives when we need them to. I also wholeheartedly believe that some people aren’t meant to come back into your life once they leave, but some need your influence, or you them, to get on the path that truly brings you together again.
We are all dynamic people that change throughout our lives. It’s unrealistic to think that the boy you meet at 16 will be identical to the man he becomes in his 20’s or 30’s. We love to give men shit for things like this, and some men deserve it to be frank, but I think people deserve the space to grow much more.
Jess is the guy that might come and go, but each time they come back it’s showing us something about ourselves that needs the microscope taken to it. He’s the kind of guy we have an unspeakably deep connection with, that understands us on a level we might not yet understand ourselves, and for all their faults, pushes us further in our story.
Maybe we don’t end up with the right-guy-wrong-time man, maybe we do. Either way, they are usually still wishing us the best as they try to do the best for themselves in the process.
Gosh, what a lineup huh? I think it’s really interesting to contemplate the lives of fictional characters, but also see how they can so easily be applied to the types of people we see everyday.
What is it they say, life imitates art that imitates life? Couldn’t be more true in this case. I’m sure there many more types of men that could be discussed, I mean we didn’t even touch the type of men Lorelai, Rory’s mother, dated throughout the series. That would certainly be a very different discussion from the one we had today.
I’m torn betwen Team Jess and Team Logan. I’ll leave that as my good excuse to keep rewatching the show, all for research!
In case that isn’t enough discourse for you on the topic, here are a few interesting articles I read to supplement my knowledge of the show, because you know, I’m only rewatching this for the millionth time.
Capsule 98 is a quick read, Refinery 29 is thought provoking, and The Polygon is just plain hysterical while hitting all the good points. Links to those are below.
Regardless, I hope you enjoyed our little deep dive into some of the would become men of the Gilmore Girls world.
Should we do things like this more often? What other shows would you be interested in deep diving into?
Have a wonderful weekend everyone!
A Series of Observations 