Rory Gilmore’s Messy Thirties: Why Her Career Failed and How It Finally Makes Her A Believable Character

[Spoiler Alert]

I’m going to say what everyone is thinking: Rory Gilmore is a spoiled brat.

Similar to Rory, I am an aspiring writer with a BA in English, but unlike Rory, I didn’t attend an Ivy League school and I had to get a job outside my field after college. Rory Gilmore had resources and opportunities at her disposal that I only dreamed about. She had top grades with absolutely no effort and rich grandparents to pay for her expensive prep school, the combination of which landed her with acceptance letters to Princeton, Harvard and Yale. She chose to attend the latter and eventually became editor of the newspaper, a very coveted position.

Rory was glorified as being brilliant, talented and wise beyond her years throughout the first seven seasons of the show. No one in Rory’s life ever told Rory no, that she couldn’t do something, or even to perhaps have more realistic expectations for eventually generating an income. No one, that is, except Mitchum Huntzberger, a billionaire newspaper tycoon and the father of Rory’s college boyfriend Logan. Mr. Huntzberger is painted as a villain in Rory’s life, but only from a single incident in which he told Rory that he didn’t think she had what it takes to be a top reporter, but that she would “make a fine assistant someday.” This feedback was given at the end of a newspaper internship that Mitchum had handed Rory with no effort on her part. Having heard no negative feedback about her career ambitions up until this point, Rory falls apart, quits Yale, becomes estranged from her disappointed mother, and moves into her grandparents’ massive pool house (which they give a $40,000 home makeover just for her). Oddly, she stays in a relationship with Logan, the one whose father has crushed her lifelong dreams in less than five minutes.

4 minute mile

The thing is, Mitchum Huntzberger had up until that point been generous and open to Rory being in his son’s life. He welcomed her and apologized after a disastrous dinner with the rest of Logan’s snobby family, and gave her an internship as an apology. His feedback to Rory, whether well-intentioned or not, stays consistent with who he is – a man who did not become the owner of a newspaper empire by telling people how special they all are, and who never even had to give Rory the time of day in the first place. Instead of taking this all into account, Rory remains completely self-absorbed, insistent that Mr. Huntzberger is out to get her. Logan tries to convince her otherwise, but Rory never does seem to get over mean Mr. Huntzberger. In one scene, after Mitchum becomes so frustrated with Logan’s reckless behavior that he sends him packing for London, Rory follows him into an elevator. “Why are you taking him away from me? Do you hate me that much?” she fumes. “You’re sending him away. What other reason is there than to separate us?” Mitchum looks like he’s about to burst out laughing. “You flatter yourself if you think I put that much energy into thinking about your relationship,” he tells her. “I’m doing what my father did for me. He pushed me, I grew up, and now Logan is going to grow up.”

I’ve had a few Mr. Huntzbergers in my life; people who have told me the harsh truth, told me to be realistic about my life, told me all kinds of things I don’t want to hear. These are the authority figures we all have, who we rely on for our wellbeing, whether they are our parents who feed us or employers who give us our paychecks or the hiring managers who decide if we got the job. At some point we have to decide to listen to what they say if we ever want to eat and make rent again. Rory had perhaps the most valuable career mentor possible available at her fingertips, and she chose to reject his initial feedback and shut down. She eventually finds her way back to Yale and the journalism department, but her tensions with Mr. Huntzberger are never resolved. At a birthday dinner for Logan in Rory’s senior year, Mitchum tells Rory that she can take her pick of his newspapers to work for. “I seem to remember you telling me that I ‘didn’t have it,’” she says, visibly annoyed.

“Things change, circumstances change,” he replies.

Years later, we enter the brand new season of Gilmore Girls to find Rory flailing around in life, failing as a writer, rootless. She is now 32 years old and is still absolutely horrible at job interviews, perhaps in part because she is so used to opportunities simply being handed to her. After a failed interview with a women’s website – which she ignored offers from for a year and then as a last resort waltzed in not expecting to have to sell herself – she expresses to the CEO how pissed off she is: “You got my hopes up for a job I didn’t even want!”

Rory displays a shockingly arrogant attitude for someone who has been apparently freelancing for the last ten years. No full-time staff writing position could possibly be beneath her, and yet here she is, scoffing at a women’s website.

And she still hates Mr. Huntzberger. Rory is having an affair with Logan, who is engaged to another woman. It is not clear whether this happened recently or has been ongoing for the last decade, but what is apparent is that Rory seems just as unhealthily codependent on Logan now as she was during college. She encounters Logan’s father one day in a restaurant one day; he walks up as she is telling Logan about a newspaper that keeps pushing back an interview. “Do you want me to make a call?” Mr. Huntzberger asks. Rory declines. After he leaves she expresses her discomfort in seeing him again, asking Logan how they managed to run into his father (the family owns stock in the restaurant, of course). What Rory still doesn’t seem to understand after ten years of ignoring Mr. Huntzberger as a valuable professional contact is that her codependence on Logan translates to reliance on Mr. Huntzberger anyway, as Logan himself is dependent on the family fortune. Rory continues to bite the hand that feeds her and is failing in life as a result.

After the disastrous interview with the women’s website, Rory gives up the job search completely and moves home to Stars Hollow, a decision that is reminiscent of her dropping out of Yale. Instead of continuing the job search, she volunteers to be editor of the Stars Hollow Gazette, a failing small town newspaper with a staff that appears to be at death’s door. Here Rory takes a first step toward humility: after removing the traditional poem from the front page for her first issue as editor, the entire town complains. Rory is resistant at first, but finally listens and reinstates the poem in the next issue. This might mark the first time in her career that she has listened to anyone, and is a turning point in her life. After one more crazed night of partying with Logan and his friends, Rory splits ways with Logan to let him be engaged – and soon afterward finds out she’s pregnant (the father is unknown but it makes sense that it would be his). While Rory’s mother Lorelai has finally come to peace with her life, Rory’s has officially fallen apart.

The fact that Rory has crashed and burned might be what finally makes her an endearing character. It took until the very last episodes of a very long show, but I finally feel like I can somewhat relate to Rory as a realistic personality; the show did a good job of finally following through with the consequences of Rory’s actions. Though I feel that the newest season is poorly written and completely misses the mark with its humor—with jokes offensive to multiple groups of people and a random, bumbling musical—it at least stays true to Rory’s and Lorelei’s personal journeys and comes around full circle. After raising her daughter as a single mom with minimal contact with her family, Lorelei is finally able settle into a happy marriage, a much improved relationship with her mother and stability for herself. And after Rory’s upbringing of seemingly being able to do no wrong, always projected to have a successful career and perfect life, we see Rory starting back where Lorelei first did: broke and with a baby on the way.

Perhaps now, starting with this new scenario of Rory needing to figure out her life not only for herself but now for someone else, we can imagine the messy growth and steady maturing of a character who is slowly becoming believable. And if Logan does indeed turn out to be the father, perhaps there is more to come in the saga of Rory and Mr. Huntzberger.


Wished-for child, one of these mornings
you’ll awake to a different light: one that listens
without speaking and acts without a sound.
These words and gestures so long demonstrated
loudly, though fragile, will soon be replaced
with a soft and constant refrain of peace.

Bitterly wished-for child, one of these evenings
you’ll rise up to speak without fear, and
your hands will rest at your sides. We will see
in you and see you: not as a working of our
exaggerated minds, but as the truth.
You are believed. And you are beloved.


I never asked to be healed from my bitterness;
only that those who see it will look to the past,
blending the roots together with earth tones.

The old remnants of harvest are iced over:
misguided acres, thick on their undersides,
frozen and steaming, desolate across the gray.
Have the invisible choirs ever seen a real bird?
Lone wings circle the field; claws skim dirt;
beak wishes for fruit to pair with fresh blood.
The farmer, cultivator of earth, has vanished
 into the thickness of haze,
tangled into the roots he planted himself,
betrayed by his own product of husbandry.
With nothing stable, a new chaos of signals,
 we grow.


The word “blackberry” looks precisely like an actual blackberry: The brown “b” is dark and damp and borders on black—earthy, composted ink running into the leafy greens of the “l” and “e” and juice-stained with the deep red “rr.” It is dusty from the dry heat, yet to be plucked from the vine and soaked cold water. I smooth the word over with my pen, releasing it to the page and letting the vines spread wild over the white expanse.

Other words match the colors of “blackberry”:

“Violin” is purple, the dark “v” velvety and thick; its throaty song sounds exactly like a blackberry tastes. The “i” and “o” are berries, small and black set against white—music notes strung along the page. The long “l” is deep green; a thorny vine; a bow scratching against the strings. The violet strains waft across fields on warm nights, soothing the earth with their voice


“Rope” is the crimson cord of Rahab that hangs still from a tree branch in the windless evening. The “r” is the dark red twist of the twine, looped into a noose and ending with a tail, allowing room for adjustment. It sits as a silhouette against the blue “p” of the evening sky and the leafy underbrush of the “e”


“Horizon” is the pink residue of the sun at dusk: the fuchsia “h” is painted in strokes across the sky, absent of golden light after the sun has sunk below the deep brown “z” of the earth. The streaks of the crimson “r” and magenta “n” blend with the purple strains of the violin and fade into the night. All is silent and still on the page and I put my pen down.

Loving Myself.

I’ve said for quite a few months now that I haven’t done well at all at loving myself; that I need to start focusing on my own self-care. It’s been definite that something needs to change, quickly. As soon as I tried to start, though, I found out that I’m pretty terrible at being kind to myself. In fact, in the last few weeks I’ve come to a startling realization that I don’t actually know how to love myself.

How is it possible to not even know how to love oneself?

As I’ve been thinking about it I realized that I’ve always assumed knowing how to love oneself is a natural thing that everyone knows how to do and that my problem is simply that I haven’t been loving myself and I just need to start. However, I’ve found the truth is a bit different: I actually literally have no clue how to love myself, because no one ever really taught me how. That sounds dramatic and terrible, but once I backtracked and thought through life it actually makes a lot of sense.

I think it’s largely due to the fact that I grew up in relatively fundamental Christianity which teaches one to not think of oneself, to “die to oneself,” to let God control one’s spirit, to lose our lives so we can gain eternal life “in Christ,” and that God loves us so our primary focus is to love God back and to love other people. The spiritually-worded catch phrases go on, but rarely is the focus on loving and accepting ourselves for who we are naturally as human beings; I’ve never heard any teaching or sermon on that during my 23 year acquaintance with the Christian church.

Of course I find all those things to be interesting and counter-cultural ideas, but ones that need to be in balance, as I feel that in hearing and having those ideas presented to me over and over by Christians throughout my life I’ve noticed a reoccurring pattern of well-meaning people almost in a panic wanting to change who I am to fit their prescribed ideas of what a good Christian is supposed to be.

As a human being trying to participate in Christianity, I have always been made by others to feel completely inadequate.

From the words and actions of others over the years I’ve been given the strong message that:

-Good Christians are extroverts, and I’m an introvert. I need to “die to myself” and “break out of my shell.” If I don’t, I’m being selfish.

-Good Christians are winsome and outgoing, and I’m too shy and reserved. I need to smile more.

-Good Christians are called to love all people, which [according to church culture] means to spend time with and be friends with as many people as possible. If I’m not spending time with people then I’m doing nothing to love them. If I’m not good in big groups of people then I’m failing. I’m literally disobeying God by not acting like an extrovert.

-Good Christians don’t get too physical in their romantic relationships before marriage. I’ve failed. I’ve been told that I’m “forgiven,” a word that carries with it that familiar pious attitude implying that I’ve failed and the other party [whether it affected them personally or not] is oh so humbly giving me some sort of pardon.

-Good Christians aren’t anxious or depressed, but trust God. My anxiety and depression is sin that stems from rebelliousness, independence and not putting enough faith in God.

Religion teaches people that they are sinners, and children are raised to believe that they are broken, were born broken, and need to be fixed. It’s been ingrained in all of us who grew up in the church. From the beginning we are never enough without God, without the church, without the massive list of things to avoid in order to be pure.

Within the narrative of the Bible and the reasoning behind it, I get it. I grew up with it, I understand the story, and have read the Bible cover to cover. But Christians are so quick to emphasize our sin and brokenness and selfishness that they don’t give people any credit ever. They say we can do nothing on our own; it’s all God’s grace and blessing. People only get in the way of God’s work and so must give up their rights to themselves in order to let God work through them. This translates into not thinking of oneself or especially not taking pride in oneself or one’s achievements. There is nothing to boast about except for what God has done. We ourselves are nothing and deserve nothing.

This background is why I have no clue how to love myself. Not only did I start out as a miserable, broken sinner, but even my natural personality is just all wrong for what’s been expected of me. No matter how hard I try, I will always mess up on most of the above points because I was just. not. made. to be a people person.

So now that I got that figured out, I’m trying to backtrack, kill the lies, and wrap my mind around that fact that who I am as a person is ok, fantastic, that I have many good qualities and have value as a person simply because I exist. I have to start sending myself strong, consistent messages to blast out the previous messages I’ve received.

I am teaching myself that:

-I am an introvert, and that is the coolest thing ever. I think about things and notice things that a lot of other people don’t think or notice. I don’t need to change anything and my personal shell has been a lifesaver quite a few times. There’s nothing selfish about being my natural self.

-I am shy and reserved around people I don’t know or don’t like, and there is nothing wrong with that. People who know me know how warm and friendly I am toward those I love. I don’t owe anyone anything, and don’t need to drain myself to reach out to every single person I encounter. Smiling isn’t a mandatory action, and there is nothing wrong with not smiling. It doesn’t mean anything is the matter—this is also a social construct.

-I don’t spend time with a lot of different people, but the relationships I do cultivate go very deep. My few relationships are so much more meaningful than having a ton of surface friendships. I show love in those relationships in ways I never could if I tried to reach out to every person I meet. It is also possible to love without spending time with multiple people, but simply my life work and what I ultimately contribute to the world can be an act of love.

-I have a huge capacity to love within romantic relationships. There is nothing that happens within those relationships that will ever define or change my value or who I am as a person. Enough said.

-I struggle with massive anxiety and small bouts of depression, and that has nothing to do with my spiritual life. I have every logical reason and right to believe those things have to do with how my brain works. That doesn’t make them ok or fun to deal with but they aren’t wrong and they aren’t my fault. There’s nothing wrong with feeling melancholy and I actually even appreciate that aspect of myself. Spirituality certainly helps with my anxiety at times, but to tell someone their anxiety is sin is spiritually abusive and no one has any right to say that to anyone, ever.

I have done my best with the religion I was raised in, but the fact is that all religion is a form of brainwashing in a way, and it’s pretty sick and twisted to raise a child to believe that they are sinful and broken. I don’t blame anyone for teaching me and my peers this; it’s completely engrained in Christian society and is a major part of the doctrine. However, with it comes shame, self-doubt, and a constant feeling of inadequacy. I don’t need to beg God for forgiveness every day for sins I supposedly committed just from being alive. I don’t need to apologize for my own sexuality and desires that come with it; I don’t need to apologize for the fact that I have a beautiful body and that I love how it looks.

I don’t have to feel shame for most of the things I’ve felt ashamed about for most of my life.

I don’t need to listen to what other people tell me is right or good. I can decide that.

It’s ok to not know where I’m at with religion right now, or how I feel about God right now. I’m going to take all the time I need to deal with that.

I’m going to take all the time I need to care for myself, to learn to love myself.

I am free to be.



Woebegone, the single symbol on the table
& our rotund laughter sounds out the word:
a sepia echo, conjuring images of yore &
macramé wreckage in the roadside ditch
—what can match it? a final breath, ceased
or fragments of a voice that never spoke,
realizations of ego misplaced from reality:
sullen sacks of loam dumped from carts—
irritations stepped over in the street whilst
we compulsively snack on jejune worries,
using our steep myopia to avoid metanoia—
revivals are for ones who read upside down
and construe the scrambled lines as certain.
Woebegone, the ochre depiction of suffrage
& our graying cacology neglects the nuance
—how to convey a meaningless ache?
Encryptions only point to the carver’s hand,
raw umber in its appeal, but its ethos is cold,
words that no longer respire but for display,
insouciant fixtures of our terminal languor.





“Some people tu…

“Some people turn sad awfully young. No special reason, it seems, but they seem almost to be born that way. They bruise easier, tire faster, cry quicker, remember longer and, as I say, get sadder younger than anyone else in the world. I know, for I’m one of them.” ― Ray Bradbury