The Longest Open Letter in the World, Addressed To Rory Gilmore, Seasons 1 and 2, Being the First of Two Parts

Hello Rory, you moon-faced L.M. Montgomery heroine, you pint-sized monster of wholesomeness, you bookish Nancy Drew. How are things? Seems like you’ve been having a lot of boy trouble over the last two seasons! Tristan wants you and Paris wants Tristan and Jess wants you and Dean hates Jess! Or at least, that how it’s spun–heartbreaks,  feuds, your inevitable and harmless Sweet Valley High teenage romantic drama.

But it’s really not.

I know this may sound strange, so let’s start with Tristan. Ugh, Tristan.  I’d be preaching to the choir if I told you he’s an entitled little toad, so lets go through some of the specific manifestations of his toadery.

-He repeatedly bothers you for a date when you’ve made it clear you in no way welcome his advances.

-He steals your school books and refuses to give them back unless you agree to go out with him.

-He publicly misrepresents your relationship and lies to schoolmates about going out with you.

-He uses your angry controlling boyfriend (whom we shall get to LATER) to blackmail and humiliate you throughout a school project that is 50 percent of your final grade.

In other words, he does his best to make school a toxic nightmare for you, either to browbeat you into accepting his overtures or punish you for rejecting them, it’s not quite clear. We have a name for this behavior. It’s called sexual harassment, and it’s something that, if Chilton receives a dime of federal money, it has an obligation to prevent and address.

Saying “sexual harassment” might sound weird, but trust me, calling these things by their proper names is much less weird than being the kind of person who would do any of them.

We both know Tristan is pathetic, but he doesn’t have to be a full nuclear, bodies-in-freezers threat for you to decide that his treatment of you is not remotely ok, that it is not your problem to manage, and that it must cease and desist immediately.

Nor is this to say that you’re not handling it well or that you’re weak. Freedom from sexual harassment isn’t a special protection for those too weak to handle it; it’s about freeing you from expending valuable energy dealing with capricious aggressions so that you can focus on your actual job, which is 100 % schoolwork and 0% Tristan’s issues. You don’t have to refrain from taking action until the problem spirals out of control because “uuugh, can’t you just be cool, why are you making us deal with this, this is so awkwaaaard for us.” People who say this, implictly or explicitly, are bad and will hopefully soon meet a fairy who makes toads fall out of their mouths.

And I know you feel sorry for his issues, and that’s ok!  But his problems do not equal marching orders for you to suck it up and think of England: you’re not a therapist, and if you were, I’m pretty sure you’d have both fees and boundaries. Insofar as you can help Tristan, it’s by not giving him a sad-rich-boy pass. Calling things like sexual harassment by their rightful names sheds sunlight on on something that thrives in obscurity; it creates room for the possibility of addressing Tristan’s behavior before it becomes an entrenched pattern that, as time goes by, grows more serious and less easily disentangled from Tristan’s character.

But at least everyone knows that Tristan is a jerk. Dean, on the other hand, barely needs a white horse to be officially crowned World’s Best High School Boyfriend, and that is why your relationship with Dean scares me more.

For your three month anniversary, Dean takes you out for a big, fancy, romantic night out, surprises you with a car he built for you, and then tells you he loves you.

Oh Rory, this is not cool. Surprising someone with an extravagant, unasked for gift that they can neither reciprocate nor politely turn down right before springing a major emotional declaration on them is hugely inappropriate.  Building her a car is something you do after you’ve both said I love you, not before you unilaterally escalate the relationship. I know we’re supposed to think that a man spending two month’s salary on a woman before ambushing her with a question that will determine the course of her life is sweet, but what Dean did here is manipulative.

And Rory, you handled it so well! You avoided the trap of going along with it, saying I love you just to make him happy. Because no matter how much you love do in fact love him, that pressure, that lack of freedom you felt will poison your relationship and make trust or honesty impossible. You were kind, empathic, and communicated your feelings and boundaries clearly. That is the kind of relationship skill that takes years to learn, and you knocked it out of the park on your first try in a terrible, high-pressure situation! High five Rory!

And Dean threw a tantrum. He didn’t say “You don’t have to tell me I love you till you’re ready, but that’s where I stand.” He didn’t say “Oh man, this is awkward and hard to hear. I’m not sure how to react.”  He didn’t say “I’m glad you felt comfortable telling me that.” He didn’t even say “I get that you’re not ready, but I am, so this is really hard to hear. Let’s take some time alone to think about everything.” He threw a tantrum, and in a minute had you apologizing for having boundaries and speaking up about them.

Rory, there is not one goddam reason you should have been able to say “I love you” back. You’re 16, this is your first relationship, you’d been going out for three months. Everything you said was prudent and right and kind, and anyone who makes you apologize for not offering up emotional intimacy on demand as soon as he’s ready is not someone who knows how to love.

And then! And THEN, a few months later, Dean says “I told her I loved her and she just sat there and somehow I’M the bad guy?” Yes, Dean, you are the bad guy, because love isn’t a prize she’d damn well better show proper gratitude for, it’s something mutual, and organic, and caring, and respectful. I get that you made Romantic Gestures, but if you weren’t ready to hear anything but what you wanted at the end of those Romantic Gestures, they suddenly seem less like romance and more like a trap. Pro-tip: If you can’t handle a “no,” don’t. build her. a fucking. car.

Rory, you did nothing wrong. I’m sorry your boyfriend manipulated and punished you, and I’m sorry the people who should have had your back the most unconditionally made you feel like there was something wrong with you, not Dean. Unfortunately, that part doesn’t really get better as you get older.

Speaking of which, a digression.

Lorelai, what the hell is wrong with you? I get that you never got an adolescence of your own and are therefore in some ways emotionally frozen at 16, but you need to get it together, and fast.

When your daughter finally tells you why her boyfriend broke up with her, your response is, “I’d hate to think I’d raised a kid who couldn’t say I love you.”

When you see your daughter freaking out because a sex-pest is threatening to tell her boyfriend that they kissed the night after he dumped her, you don’t say “Honey, let’s  bracket for a moment our discussion about sexual harassment and what steps you feel comfortable taking.  The fact that you are so worried about Dean’s reaction to something that happened after you broke up, when you were completely free, and which is absolutely none of his business in the first place—it is starting to worry me. Hearing this might be painful for Dean, but in a good relationship it shouldn’t engender this much stress.”  Instead, you say “This is the kind of honesty that will only make you feel less guilty, and it’s going to hurt Dean very much,  and possibly going to screw up the very good thing you guys have going now.”

When you see your daughter going out of her mind with anxiety–not sadness, not distress, anxiety— because she accidentally lost the bracelet Dean gave her, does this raise any red flags for you at all? Nope, you just help her look for it and yell at Jess for taking it.

When Dean calls, what, 16 times in one day? do you say to Rory, “Wow, that is intense. How do you feel about this? Are you ok?” You say, “Honey, you’ve got to ease up on that love potion you’re giving him.”

You are telling your daughter that living in fear of upsetting your boyfriend is normal, that angry jealousy and failure to respect boundaries is par for the course, and that if her boyfriend starts behaving in ways that make her uncomfortable or miserable, that it’s just because he loves her so much. Do you have any idea idea how messed up this is?

True, you do tell Dean to give Rory some space for the sake of her relationship, but whether or not their relationship works out is not what worries me, and it sure as hell shouldn’t be what worries you. What worries me is Rory learning that love means a knot of anxiety in the pit of your stomach, and that romance means refusing to leave you alone or give you space. It’s the possibility of this learned identification of love with control haunting her for the next 20 years as these patterns become hallmarks of all her relationships. I’m afraid her ability to speak up for herself and listen to her gut and identify problems is slowly eroding–and I can already see it happening. And because all the advice you give her is about conisdering Dean’s feelings, managing Dean’s jealousies, learning to prevent his anger, she is learning that a) all these things are healthy and her job to take care of, and b)  that the goal is always keeping your boyfriend, no matter how miserable he makes you.

She’s just beginning to learn what love and relationships mean, and you are her first and final baseline of normalcy. You are the one who sets the rules of what’s ok and what’s not in her world; you’re the one she trusts to give her advice on boys. You don’t need to forbid her to see Dean or sit outside with a shotgun, but you do need to check in with her–not about how her relationship with Dean is doing, but how she is doing. You need to be the one who offers her a vision of healthy relationships, who helps her talk through feelings of fear and powerlessness and unhappiness and give them names, who reminds her that she is a person before she is a girlfriend, who lets her know that she is loved and supported and that you care for her, not her-with-Dean.

Stop advocating for your daughter’s relationships and start advocating for your daughter, because she needs you, and you are blowing it.

End of digression.

Anyway Rory, turns out I’ve a lot of things to say about the boys in your life, so I’m going to call this Part One and wrap it up here. In Part Two we can chat more about handsome handsome Dean and handsome handsome Jess, and why you should flee them both like peasants do a plague ship.

Until then I remain,

Yours faithfully,

Cranky Aunt Clare

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