How to: Write a Thank-You Letter to a Mortal Enemy

Jesse Stewart
33 min readJul 13, 2020

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Delacroix, 1862

You want to start with a pleasant salutation; “Dear so-and-so” opens the gates a little wider than, “Hey Dickface.”

Alexander Pope once said, “To err is human; to forgive, divine” and an old proverb warns that “Before embarking on a journey of revenge, dig two graves.” These are fine cereal-box axioms, but in matters of honor for the practical person, I dive for the words of Malcolm X:

“[…] be peaceful, be courteous, obey the law, respect everyone; but if someone puts his hand on you, send him to the cemetery.

A ‘mortal enemy’ is not someone you’re annoyed with or a person that gets on your nerves, it would be a figure whom you’ve harbored a great hatred toward for a long time. I believe most people aren’t misfortunate to have someone like this in their lives, but occasionally a certain person transgresses in a certain way which then becomes encoded into your DNA. You may never cross paths again, dooming you to hold hypothetical arguments in the shower until the memory fades and your hatred dissipates, until you accidentally scrape that scar a few years later and discover that your ire is now, like uranium, enriched.

You might have the desire, and in rare circumstances the open opportunity, to write to your life’s antagonist. Maybe your foe reaches out first, or perhaps an appropriate chance presents itself. There are nearly a million ways to write this kind of message, and most of them are wrong. Perhaps this person is a former lover, or a business associate, or someone you wish you could still call a friend, and therefore you can’t come across as brash or unprepared. Given the chance to finally air your grievances, it’s important to hold a conscious quill for your poison pen letter, as you want the ink to stain their fingers but not bleed through the pages and render your rage illegible.

My mortal enemy is a man we’ll refer to as ‘John Doe.’ I would relish the opportunity to publicly drag his real name through the mud as if I were pulling the man himself behind a horse through a muddy town square, but his actions affected more than just me and I must protect the privacy of my fellow transgressed. It would be disrespectful and inappropriate to specifically detail the man’s actions that caused me such loathing, as I respect his general human rights as well, but I had two opportunities to file complaint with his general existence and therefore have some experience with which to help you in conveying your thoughts to your existential adversary.

Presentation

Before even thinking of what you’d like to say, consider the aesthetics of your note: should it be handwritten or typed? There is a difference and you’ll need to make a good first impression, as the visual language of your objection is just as important as content itself. For example, John is a bit older than me and has an ironically-low reading comprehension, so typing his letter was an obvious choice, made even more easy by the fact that my pissy penmanship wouldn’t be all that pleasant.

Handwriting your vexation is best if you wish to be truly personal, which is only appropriate if intended for lovers, family, or friends, as your ‘font’ showcases your personality in ways that the reader must already be familiar with. Carefully consider what ink to use before putting pen to paper; black or blue sets a good tone, but I’d advise against blood as it actually dries brown.

Salutation

There are so many ways to re-introduce yourself into the monster’s dungeon, but it’s hard to go wrong with the tried-and-true, “Dear ______,” as you don’t want to put too much attitude toward the beginning of the letter. “You catch more flies with honey than vinegar,” as they say.

I first met John under exceptionally-precarious circumstances, as he had already transgressed against me in a purposeful way. He knew of my existence, who I was and what I stood for, and did something that weakened my personal and professional relationships at the time, simply because he didn’t like ‘the idea’ of who he ‘thought’ I was. It was one of the ten worst things anyone had ever done to me. But, when I met him at a coffee shop to ‘settle things,’ the first thing I did was hug him.

In life, it is important to be as nice as possible, as thoroughly and often as possible. The majority of this desire should come from wanting to express yourself through ‘goodness,’ to better many lives with positive interactions…but this inclination also provides you a minor detonation code to absolutely obliterate anyone you come in contact with, should they choose to be greedy.

As a confrontation between any two people is possible, you should always be able (if need be) to stand comfortably in a position where the other party is forced to confront the fact that they wove the rope that they’re now hanging from. Try to consciously act on what the most considerate option in any given situation is and allow the other person ample opportunity to make their choice, knowing that you can always claim to have made an attempt to keep their best interests in mind. My brother didn’t coin the expression but I constantly take his advice to heart: “Don’t do or say anything in the moment that you’ll have to apologize for later.”

You shouldn’t base your actions on anything other than an intrinsic desire to see other people happy, but don’t refrain from acknowledging that ethics and morality provide wonderful counterweights to hang immature people with the instant they lay a metaphorical hand on you.

The first time I met John was to confront him about his wrongdoing, each of us now aware of the others existence and our inability to operate very far from one another. He made it a point to say how he refused to apologize because he ‘believed in’ his actions. That was his agenda. Mine was to hug him hello, buy him a muffin, talk about his childhood, and hug him goodbye. In regards to some form of ‘masculinity,’ it’s easy to say that he ‘won’ this ‘confrontation,’ as he didn’t ‘back down’ from his stance and I technically ‘yielded’ to my transgressor. But life is not a game of checkers, or even chess: it’s protracted guerrilla warfare, and the long game is the only one that matters.

Casus belli’ is Latin for “the occasion of war” and it essentially measures the ‘validity’ of a conflict. The German casus belli for invading Poland was ‘regaining lost land’ that was ‘taken’ from them after World War One, but this was not recognized as a ‘just’ occasion for war by the rest of Europe. Compare this to the American casus belli for going to war against Japan: they struck an unprepared and un-notified America first, making America’s ‘occasion for war’ comparatively more ‘just’ in the eyes of the world. A casus belli is subjective, but only in varying degrees.

In meeting John at that coffee shop, I wanted to be his friend. The meeting was on the other side of the city: I wouldn’t have gone for any other purpose other than establishing a bond. I had no intention to hurt or get back at him, I didn’t have any time or desire for that. We had similar interests, got along well enough, and even made each other laugh. I knew he liked apples, so each time I saw him from that point on I usually had an apple to give him. Like anyone else, I saw him as a person that could teach me and an avenue by which I could produce more ‘goodness’ and love in the universe.

I planted a seed the day we met, one that would inevitably grow into a tree: if we got along well, then we could enjoy the shade and apples together; but if we didn’t, it wasn’t going to be because of my behavior and it would provide him a strong branch to hang himself from.

Greeting

Open your letter with well-meaning questions about their well-being, built it from the lumber of whatever tree you and your mortal enemy have grown together. This can be difficult as, again: you cannot be passive-aggressive, sarcastic, or inauthentic. In writing your letter, and specifically your opening statements, you must express honestly and genuinely that you do care about the other person. Concern about another’s happiness and state of life can be quite difficult when you also want to see them dragged by their ankle from behind a muddy horse, but it’s an easy process when you do your homework.

Love and hate inherently stem from the same place, one can only exist in some way because of the other. Let’s say you’re driving on the highway and someone cuts you off. Even the most rational person will still be relatively incensed by this senseless action. But, if questioned, would you say that you hate the person in that other car? Very likely not, as you don’t even really care about them. They’re just another person in the world and the odds are actually astronomically-low that your paths will ever cross again.

But that romantic partner? That co-worker? That former friend? That family member? The only way you can hold onto a profoundly negative feeling about a bond is if, at one point, it held you in a profoundly positive way.

You can’t write a poison pen letter if you don’t, to some extent, care for the other person in a constructive way; you’ll only end up pricking yourself. You may think this is your outlet to get revenge, or ‘make things right,’ but the reality is that you’re reaching out because there still exists some part of you that wants the best for that person. It’s a very uncomfortable thought, I know.

For my letters to John, I used the greeting as an anchor point for the noose he tied, a simple sort of reminder to him, “Oh, right, Jesse has been nothing but kind to me and this entire situation is exclusively my fault.” It is very important in your letter to not come across as passive-aggressive or sarcastic, there is no stronger braid for that rope than staying authentic and true.

John is a particularly unintelligent man who takes out his deranged insecurities on those who lack the sense to escape his orbit. In retrospect, he and I bonded because I saw him as what I could become someday if I were to let my dumbest vices justify themselves. He is a man who, only until very recently, believed that one must be miserable and unhappy in order for their art to be ‘real.’ You know, like a fourteen-year-old. He would be a talented writer if he weren’t self-sabotaged by arrogant compulsion, but I could at at least acknowledge that he subconsciously imparted some invaluable knowledge to me about how to fix the errors and hangups in my own work.

In many ways, I thought we could have been friends for a long while. Like I said, he is older than me and will likely pass away long before me, so I figured we would be friends for the rest of his life. We both wrote screenplays, stories, and poetry and were able to trade our work with one another for valuable insight and perspective. But there was a small and unspoken contempt between us, stemming from his insecurities; this was likely because we could be similar in our intents but radically different in our actions (i.e. I followed through on every promise I made).

When asking how your mortal enemy’s life is or stating how well you hope things have been for them, it is paramount that you actually mean what you write. If you are insincere they will be able to smell it: your words will come across as false and untrue to the ‘you’ that they know. And they do know you to some extent: you will have had to let them into your heart in some way, because otherwise you would not see this as an ‘opportunity’ or ‘chance’ to communicate to them.

Statement of Purpose

After your opening remarks, avoid the scenic route: what is the context and purpose of this communication? It can be a long laundry list recounting their crimes, or a simple statement of displeasure; we all like to be ‘heard.’ Don’t feel the need to be so direct, but always be aiming toward ‘the point.’

John and I shared many meals and hours together. We spoke as friends, confiding in one another, as well as working alongside one another on creative endeavors. He bought me a chocolate-chip muffin on the day of one such project and I let him know, many times, how much I appreciated that specific gesture.

If there’s one thing I’ve learned in my years it’s that time shared is never guaranteed, so you should make your feelings about someone known while they’re present. I frequently start heartfelt statements to lovers, friends, and family with, “There’s no way of knowing if one of us will get hit by a bus tomorrow, so sorry to make it awkward but I need to say this: your socks are so cool and I’m so happy you’re in my life.” I’ve had far too many that I treasure die without knowing how much I loved them so now I verbalize my feelings, perhaps more than necessary but I’d rather have that than any more of the opposite.

I would profess my appreciation often with John. I understood that the genesis of our bond was very atypical so I put in the work to make him feel seen and heard as a human being. Sometimes he reciprocated this, other times he grew vindictive. He would often gaslight me in front of others. We might deliberately discuss something in private, setting all the details straight, and then he would purposefully put me into public situations where he would ‘change his mind’ to watch me squirm in ‘fixing’ the problem. I think he continued to associate with me because I was a bit too decisive and improvisational to ever ‘squirm,’ so I became a challenge to him. Like any bond, the unhealthiness of an interaction doesn’t quite become clear until time and distance boil away the minor good elements that may have been a distraction. No chocolate chip muffin could make up for a lack of trust (though do let me know if you find one).

Ultimately I would later discover something about John and I’s bond that caused me to pull the rope on his noose, quickly and without guilt, and I think he was surprised to discover just how high up I could hang him.

He had made a promise back when we first met, one that I warned him he would need to work to keep, where he laughed that I would dare question his reliability. But I discovered a year later that not only had he broken our promise but actively worked to continue breaking it. Behind my back and lying to my face, he had exploited my goodwill and kindness to appease his insecurities and greed: he needed to ‘win.’ So I metaphorically strung him up by our metaphorical tree. There were no apples on the branches that day.

But after his execution, I was mired in my pesky ‘get-hit-by-a-bus’ ideology: I had bought him a heartfelt gift before I discovered his deceit. Like having a tickled nostril but being unable to sneeze, I don’t like my ‘good deeds’ to go unfulfilled, even if I no longer feel how I once did. I resolved to have a mutual friend deliver the gift, as well as a final letter to him.

It was at this point that I understood I now had a ‘mortal enemy’ and it made me feel childish at first. I have a pretty good memory, which makes it easy to hold grudges, but I don’t like to cling to such things because I’m rather sensitive and sentimental; resentment burns a hole in me somewhat quickly.

But I had never felt so negatively about a person. To this day, I wouldn’t call it an active thought but I do take the existence of this person as an odd ‘motivation’ in life. I carry some weird subconscious comfort that he will one day be gone and that the world, no matter how genocidal, reckless, and indifferent it may be, will be even just slightly better with his absence. Like I said, my feelings were reduced to a very juvenile bitterness.

I had no intention of letting him know the depths of my reaction, or to recite his sins. The fact that I had so quickly strung him up by way of immediately ceasing all contact made my point very clear. No, I was burdened with an unusual task: I had to write this pathetic man a thank-you card, as I needed him to understand that I didn’t take him for granted in the way he did me.

This could have been done in a very sarcastic or ironic way, but I knew I would lose his attention. I knew the soldiers at his gate wouldn’t let more than a sentence or two into his heart. A more malicious person than I would have fashioned some kind of Trojan Horse in order to ‘trick’ him into reading most of the letter, only for my ‘true’ feelings to come out by the end and stab him. “Et tu, Jesse?

No, I knew I had to throw a parade for the tyrant so that he could see just what it’d be like when one of his freed indentured servants made their compassion irreplaceable, only to defiantly escape his orbit like none had before. In attempting this endeavor, I was lucky enough to already have some experience in learning how to turn the other cheek when confronting ‘monsters.’

When I was a child, the name Warren Simms was the most profane thing one could possibly utter. “Do not say that around your father.” “Do not bring that up at your grandparent’s house.” “We do not talk about Warren Simms.” Simms was not my mortal enemy, but he was more real to me than any Darth Vader, Voldemort, or Satan ever could be.

My grandfather was a laborer from Oklahoma, my grandmother was a worker from Missouri, they were both born into total poverty at the start of the Great Depression. My grandfather never exercised a day in his life but was in peak physical condition due to his strenuous construction work. My grandmother, though renown for her kindness, was notably aggressive about running a clearly desegregated daycare service out of the family home. If my grandparents were anything, it was hardworking, virtue-minded, and poor.

In the 1950s, my grandfather scouted the Rocky Mountains and found gold. He carved a road (by himself) up mountains, across ridges, and into a valley. He started a company, hired workers, and dug a mine. This was all born of his own ambition, volition, and through little means other than elbow grease.

He and my father would spend summers up in the valley with the miners as they extracted gold ore from the mountain. It was a relatively profitable venture, but it did not elevate the family to the middle class. My aunt and uncle grew up without much, as well as my dad, but they made ends meet.

By the 1980s, my grandparents were in their sixties and needing to retire, my grandfather could no longer stomach the high elevation and his body was ravaged by a lifetime of labor. The mine was doing well but not well enough to retire from, so they looked into selling their ownership in the mineral they found and the company they had founded.

Enter: Warren Simms, a broker in the effort of selling the mine. Not much was ever said about Simms’ appearance other than he was not a ‘worker’ in the way that they were, and that there was something uncertain about his eyes. I will be thirty years old soon enough and still feel a tiny dread in my stomach when remembering the pause that my family might put into that description when telling me as a child, as if we were talking about some force that caused them great pain, their polite smiles fading, “His eyes were…uncertain…”

Simms found buyers and facilitated the process of transferring ownership in the mine. It’s unclear exactly how much my grandparents would have earned from the sale, but they would have been millionaires (and that’s not adjusted for inflation). For two frugal, Great Depression kids, a million dollars might as well have been infinite, but they only thought of their children. By this point, my aunt and uncle were middle-aged and fine, as they were born many years before my father, who (like my grandfather) then worked manual labor in construction yards and oil refineries, acquiring similar injuries in the process. I had yet to be born but this sale would have elevated the status of the family to the a place equal to the hard work they had spent a lifetime putting in, an opportunity rarely provided to anyone in the lower classes of America.

But, just as all parties approached the table to sign on the dotted line, Warren Simms pocketed the money and ran. He disappeared from the face of the earth. Untraceable. The investors were out a fortune and my grandparents couldn’t technically operate the mine anymore. Just like that, the better part of three decades of work and determination washed down the stream; gold may settle on river rocks but dollars only float away.

Just after I was born, my father was fired from his job at an oil refinery, a place where many friends died, as “the place ran on luck.” He had developed a minor on-the-job disability and had to sue the company for wrongful termination while simultaneously starting his own one-man business. I grew up somewhat middle-class, but my holiday memories are of his snowy boots walking across the old green carpet to kiss me goodbye each Christmas morning because he never had a day off. My grandfather died of cancer in an inadequate hospice because we couldn’t afford better care. I couldn’t go to a university because we just didn’t have the money for me to be comfortable doing so; I worked manual labor with my father in order to pay for community college. My father, now in his sixties, likely can’t retire for quite some time.

We don’t really curse in my family but just about any word in existence would be more welcome than uttering the name “Warren Simms.” My grandparents were never outwardly vindictive, I think they were a bit too sweet and accustomed to hardship to be broken up about it, though my father always said that the wind never quite returned to their sails after the theft. My aunt or uncle might grow silent after hearing the name, we cousins know not to bring it up. I haven’t said that name to my father, who was party to the ordeal, in a decade or two, for fear that it might take the remaining breeze from his older sails as well.

My life would be infinitely different had that money entered our lives. It wouldn’t have been enough capital to corrupt the family, as they’d only be moved to ‘upper-middle class’ at best (no one would have inherited anything substantial until my grandmother’s death in 2016 anyway). But my grandparents could have actually retired, my father wouldn’t have been put in a vice as a new parent facing the death of a career, and I could have pursued the academic endeavors they all wanted for me. Three generations of sustenance, wiped out in an afternoon by greed and exploitation.

No one knows where Warren Simms went, or what happened to him, but there is a legendary family story of one summer when my father went up to the valley and just so happened to run across his mortal enemy.

My father is a very verbose storyteller, choosing to let you know every little superfluous detail of each event he recounts. But in the few tellings of the evening he ran across Warren Simms, he always grew very quiet and was incredibly consistent with the specific details. My father is a jolly and generous man, but he has a capacity for force. He was a football player in his youth, attracting the attention of the Green Bay Packers as a high school student, only for his opportunity to disappear with the arrival of too many concussions. He spent a few years in disarray, with plenty of stories about the fights and altercations of a reckless youth. He is kind, but with the capacity for force.

The story goes that my father was in the valley, camping, and drove up the narrow road that my grandfather carved only to encounter another vehicle traveling down the road in the opposite direction. This is not uncommon in most mountain roads, where one vehicle must to pull over for the other to pass by, but this valley is particularly secluded. When both vehicles stopped, my father saw Warren Simms himself, looking slightly “different from before,” sitting in the driver’s seat with a younger woman in the seat beside him. My father surmised this woman was his girlfriend, not the kind that ‘money could buy’ but clearly not interested in Simms for his uncertain eyes.

Both men exited their cars. My father would usually become quiet at this point of the story, saying something ambiguous about there not being anyone around for miles. I believe that he meant that this was expressed to Simms as an intimidating statement, but his phrasing when recounting the story was always very calculated and specific. Apparently the two exchanged a few words before my father said something that “made his girlfriend go pale” before expressing something different to Simms which caused him to lose the same color in his face.

In my mind, when imagining some great confrontation between ‘good’ and ‘evil,’ I don’t see a knight fighting a dragon in a cave or armies facing one another; I see my father and Warren Simms standing on the destitute road my grandfather had built; and when I found myself tasked with confronting my mortal enemy, I looked to my father’s actions in that moment for guidance.

My father is a hunter, an avid sportsman with no shortage of firearms, especially at that time. It’s not as if the FBI were searching for Simms, but he was exceptionally off-the-grid and unfindable; when someone steals a fortune, usually people are more than a little eager to do some digging. In some alternate universe, my father could have easily taken a much darker path when faced with that impasse. The valley is nothing but isolated. Maybe his action would have been discovered someday, but not for quite a long time. But I think he knew then and now that such an action would not have made that mountain road any less destitute nor bring any sustenance to our lives.

He always ended the tale with the same general sentence, “I pulled over and watched him as he drove down the mountain, still white as a ghost.” My father was the one who made the effort to acquiesce, not Simms. It was not that he ‘submitted’ to his transgressor: he gave his enemy a path of retreat by which the only way to travel was to slither.

I relate this extended bit of Stewart Family lore to emphasize a point that your letter should uphold: not a single word should betray your ethical or moral high ground, but the intention of the combined effect should be to drain the color from their face and force them onto their belly. You are to create a memory that they will be unable to suppress.

People genuinely think of themselves as ‘good’ no matter how atrocious their deeds may be. We judge others by their actions but are much kinder in how we see ourselves, choosing only to evaluate our intentions. Another old idiom states that, “The road to Hell is paved with good intentions;” often this is where we can condemn ourselves to, unknowingly, by not being honest with how we’ve hurt others.

Your letter to your mortal enemy should be a favor, an opportunity to teach them a new lesson and a drastic avenue to be a good influence in their life, even if only in one final instance.

You can be aggressive and combative in your writing, and that’s probably warranted, but what end are you searching for in this situation? If you’re just venting: monologue in the shower, or ask to talk to a friend. What pragmatic solution are you hoping to achieve in all of this?

John is quite possibly the most pathetic person I’ve ever met in my life, certainly the most despicable, but I probably wrote two or three sentences of my poison pen letter before realizing that I actually felt sorry for him. I then attempted to adopt a new perspective, one that questioned what must have happened in his life for him to behave in the way he did. I was old enough to know that his behavior would be punished eventually, someone less merciful than I would come along and darken his valley with a more significant action.

It is in the distinction between the mountains of Forgiveness and Mercy where you must build the cabin to write your letter.

Make no mistake: I did not and never will forgive John for what he did. He’s an absolute rat and this universe will be all the better when he’s gone. I will never feel joy at the death of another but if I ever learn of his passing it’ll certainly be the shortest mourning of my life; the dirt upon his grave will be packed by my dancing feet.

But I have no other feeling than mercy for him. In my mind, he’s like some kind of primordial shellfish, scuttling along the ocean floor, searching for scraps of validation among a generation of unrecyclable garbage. I could crush him and appease my emotional compulsions, but for what purpose? What use is there in squashing something small just because it hurt you? In following a compassionate moral and ethical code, you are ‘bigger’ than your mortal enemy; if you resort to the same framework that allowed them to transgress against you, you will find yourself dwarfed by inexperience.

A coked-up mining broker blew apart three generations of my family’s livelihood and it made me who I am today. I wondered what happened in John’s life to make him act in such a way, and I found that the tides of my anger eventually subsided and a mist of sadness hung in the air. It’s not that I wasn’t enraged at what he had done, but simply more sad that he spoiled a profound opportunity for personal growth.

I thought we were in an alliance, but he had simply moved a big wooden horse into my fort in referring to us as, “Not just friends, but brothers.” He managed to slaughter some of my favorite soldiers, but to what end? John’s casus belli against me was based on nothing but insecurity and projection. His was not a just war. I’ll always have that over him, his insecurity over acting in bad faith will lacerate him deeper than it ever cut me.

Did his actions grant me a legitimate casus belli against him? Absolutely. Did my mind immediately race with possible retaliations and counter-strikes? Of course. Did I not have every means by which to rain some degree of hell upon him, knowing his exact vulnerabilities and weaknesses through a year of ‘brotherhood?’ Sure.

But the most important question you’ll face when drafting your declaration of war against your mortal enemy is this: which hill is it that I want to die on?

My grandfather carved a stripe through the impenetrable Rocky Mountains to elevate his family from destitution; but didn’t want to die fighting for that hill. My father watched his father’s work be senselessly stripped from him and his son’s future called into question; not only didn’t want to die on that hill but didn’t feel as if anyone else need to. John royally exploited my very nature and did some degree of psychological damage that I’m still recovering from; but my ambitions and standards in life dictate that I should die on a hill much less pathetic and pitiful than John’s.

So, by the end of my statement of purpose, I pulled over to the side of the road and let John drive by, draining the color from his face with a, “But I do love you and appreciate all of the help.”

Closing Remark

I often default to humor or something unexpected when I reach the end of a piece of writing, but I wouldn’t recommend this for your poison pen letter. Your mortal enemy probably doesn’t deserve a laugh. It’s not a good idea to end on a note of levity anyway; it might be in your nature to ‘defuse’ tension or awkwardness but in doing this you’re actually lubricating their noose. They took a lot of time in crafting their demise, let them have it.

Conversely, you also shouldn’t take this moment to tighten the rope around their neck. Refrain from dropping any ‘bombshells’ or saying anything particularly inflammatory. People typically best remember the ending of something more than the previous sections, so don’t undo the efforts and intentions of everything you’ve crafted beforehand by ‘sneaking in’ a ‘mic drop’ moment. Stay true to the tone and message you’ve set beforehand and it’ll just drive the point that much deeper into their heart.

The end of your letter should reflect your feelings on the relationship you and this person had, have, or you would like to have. Again, this comes at some expense to your ego. You cannot behave as if the entire bond was toxic and bore no fruit whatsoever, don’t be delusional. Grow up.

The last time John and I ever saw one another (before the falling out), we shared a particularly good breakfast at some quiet restaurant; we talked about literature and laughed loudly. He insisted that he pay for the meal. We spoke about playwriting and I managed to glean some invaluable insight (like everything else: it was in doing the exact opposite of everything that he preached, but that’s beside the point). I felt it necessary to tell him at the end of my letter of thanks that I enjoyed that particular morning, and that I hoped I had taught him something during our friendship.

But I’m no saint: I knew that all this would knock him on his butt. I have a good memory and he’s an idiot; he’d see my letter and raise his fists to fight but would have no protection for genuine appreciation and kindness. The key to any magic trick or boxing bout is to control what is expected; true compassion makes for a hell of a left hook.

What you’re trying to do in this letter is display a clear comparison: if you’re truly upset by what your mortal enemy has done, then showing just how ‘honorable’ you are will render them completely defenseless. The pathetic shellfish pinching your toes isn’t inherently smaller than you: you make it small through nobler action.

Signature

This is where it’s fine to twist the knife. You’re only human, hit them with a zinger. Be nice you yourself; you’ve been disciplined and restrained this whole time, go ahead and fire off a shot.

I could practically hear when my torpedo struck John’s battleship. I wasn’t anywhere near him whatsoever, but I could feel the air reverberate with the shockwave of my signature smacking him. I made some cheeky inside joke, referencing the first email I ever sent him, which warned, “If this goes bad, it will be because of you doing this certain thing.” So, when it went bad because he did that certain thing (albeit in a manner and degree that I never expected), I let loose a nasty little punchline to a joke that I set up a year earlier.

Like I said; I planted the seed, watered the tree for a year, and he chose to reach for some fruit he shouldn’t have, so I punted the stool out from under him. This wasn’t any sort of premeditated effort; I legitimately cared about the bond, so it wasn’t all that difficult to recall the start of it all.

The funny thing about your mortal enemy’s noose is that, if you’re nothing but kind and loving to them, it’ll be tied in the shape of your signature. So go ahead and break out the fancy quill and make that feather really dance when signing it. Don’t be petty, but it’s okay to be a little pretty.

Preparation for Delivery

Regardless if yours is a letter or an email or a text: proofread it to death. Go over it at least six hundred and sixty-six times, as the last thing you need is to come across as unintelligent or unhinged due to a spelling error or two.

Think about the method of delivery. If you’re mailing it, fold the paper(s) carefully and make everything about your presentation very deliberate and considerate. This your last volley into their castle walls, if you will. You’re loading words written in passion into a trebuchet: it’s not going to do you much good if they scatter in the wind like confetti. No, you want to have it packed tightly, so it crashes into their little shack like a dead cow plummeting from the heavens.

If it’s an email or text, premeditate the hell out of the time of day that you intend to send it. Like I said, mine was literally a letter, so I didn’t have this strategic luxury, but consider the words of Sun Tzu and his infamous Art of War when choosing when to pull the trigger on your message:

“A whole army may be robbed of its spirit; a commander-in-chief may be robbed of his presence of mind. Now a soldier’s spirit is keenest in the morning; by noonday it has begun to flag; and in the evening his mind is bent only on returning to camp. A clever general, therefore, avoids an army when its spirit is keen, but attacks it when it is sluggish and inclined to return. This is the art of studying moods.

Read the room. Send moods. It is not that you should strike when your mortal enemy is least expecting it, but when they are least able to mount a reflexive and over-emotional reaction. You will not destroy your enemy with some words on a page, so abandon that desire entirely. You will not ‘win,’ they won’t admit total defeat, and both parties will suffer casualties in this altercation. But, if you wait until the conditions are just right, your words will stay with them. By being direct, your thoughts will pierce their skin, but by being honest and warm, you will create a barbed arrowhead that they will be unable to remove. Think about your hook and consider using the date or time of day to your advantage; wait until the wind blows in your favor.

I wasn’t in control of when my poison pen letter would be delivered but I certainly had a hook: the gift. In my travels, I found a poster for a stage play that I thought John would enjoy hanging on his gaudy walls. Based on our wonderful breakfast that one particular morning, discussing literature and playwriting over pancakes, I knew that this would be a good gesture to strengthen our friendship. After the falling out, I knew my letter would be the perfect Enola Gay to deliver it to him.

Goethe’s Faust is one of the greatest plays in history. It tells the story of an intelligent man, Faust, who grows unsatisfied with life and makes a deal with Satan to acquire unlimited power and knowledge in exchange for his soul. Faust is greedy with his newfound abilities, ruining the lives of all those around him. But these figures manage to make it into Heaven because of their good actions in spite of their strife, whereas Faust is dragged to Hell, unfulfilled, when the terms of his agreement with Satan expire.

I bought a beautiful poster for John of a Faust stage play, purchasing it simply because it was relevant to what we discussed at that breakfast, but it then became the perfect atomic bomb to accompany my letter. If John was even remotely as intelligent as he thought he was, he would recognize this perfect metaphor for his actions and be devastated by it. And if he wasn’t clever enough to understand the message, then he would understand that he didn’t ‘win’ this final battle in our war of wits.

It’s not that my mortal enemy had ‘uncertainty’ in his eyes, but I often refrained from looking at them for too long as they filled me with the same uneasiness that I might feel when looking into the eyes of a shark. John’s irises might have given him a superficial charm but I had never met someone with less light behind their eyes. They were uncaring, indifferent, and cold, like those of a reptile. Even in the blackness of the jungle, one could look into the pupils of a hungry tiger and see a warmth and a spark in their leer, but John’s eyes offered no suggestion of a soul. Between his eyelids all I saw were teeth in a malevolent void (and this was before the falling out).

As I departed his life and jettisoned him from mine, I imagined and maybe hoped that my little letter and gift might split the atom and kickstart his heart, warming his bones for the first time in however-many decades. Foolish thinking, I know, but it gave me a sunset to ride off into.

Holding Period

Even after you’ve finalized your letter, hold on to it for a few days. Don’t send it until you’ve almost forgotten that it even exists. Microchips must be made in rooms free of any dust whatsoever in the same way your letter should be vacuum-sealed of any irrationality or hysteria. “Don’t do or say anything in the moment that you’ll have to apologize for later.”

My letter was delivered without confirmation or acknowledgement. I didn’t think about John for a long time. He definitely didn’t think of me either; he never did when we were friends, what would prompt him to at any point in the future?

A year later, our mutual friend attempted to put us in contact with one another. John reached out first, with the most pathetic email I’d ever received in my life (which was very ‘on brand’); just the most self-congratulatory nonsense masked as self-deprecation, the least apologetic apology to ever exist. Something like, “I’m sorry I did whatever; I’m just such a poet.”

I am but a man, so I had an extremely emotional reaction. Writing isn’t all that laborious for me, so I wrote him a lengthy response. As I said, my memory is pretty decent, and I keep a detailed journal-

-so I was able to rattle off an insane list of his transgressions. I was about ninety percent through my novel when I realized, “There is no reason you’d be doing this if you didn’t inherently still care to some degree. Why do you?

So I withdrew my troops and regrouped. “Do I want to die on this hill?” “Why do I care? For what reason?” I then realized my reaction was entirely egotistical. I was annoyed by the fact that I was cartoonishly nice to someone, who was cartoonishly mean to me, and he hadn’t learned from the lesson I so graciously taught him. I filed through the memories in my mind, both good and bad, and searched for the best response to his letter.

You must be prepared for a response. It may not come right away, it may take ten years; but it may come. Take your time to consider potential hypotheticals before sending your initial message. Do not have any expectations but understand that your letter will not be the ‘last word.’

I found the old email I had sent to John just after our very first coffee shop meeting, where I had outlined what could possibly go wrong with our interaction if he wasn’t careful. I elected to not respond to his ‘apology’ letter with new writing of my own, but to simply forward my now-‘prophetic’ words to him. The initial thought was to bold each relevant section where what I had warned against did indeed come true, but that would mean that most of the entire document would be bolded.

Like some sort of lawyer, I relished the process of reading through my old words and cross-examining them with his ‘apology,’ feeling nothing but complete vindication: every part of his ‘sorrowful’ letter carried the subtext, “Who could have possibly known this would happen and in this way?” and it was just so satisfying to kick the stool from under his feet and watch that tree branch shake when I forwarded him, with no explanation, my warning from years previous. I scrambled my jets and buzzed his tower one final time in hitting send on that email, with no other words that that old date sending the subtext, “Gee, I don’t know, John: who could have possibly guessed?

I did not receive a response. A snake does not like to be reminded that it slithers. The war was over. For now. There was no parade, no celebration, and no great victory. There were no survivors. For now.

I would have preferred to be friends with John, truly, but this wasn’t possible and the revelation of that to him was the intent of my writings. In the grand scheme of things: you, your mortal enemy, and your feud are completely meaningless. In one hundred years John and I will both be dead and it’ll be as if the entire ordeal never even happened. There will be no trace of any warm bond or cold confrontation between us. We will be equal, silent bones in the dirt, no longer holding vices and virtues but the brittle residue of unknown memories in pockets where marrow once sprang…

Stamps

Be creative and pick a cool stamp to mail your letter off with! It’s the first thing they’ll see when receiving it and the final image they’ll note before throwing the envelope away, so pick something fun! Look at these peanut butter and jelly ones, aren’t they sweet?

Sending Your Letter

You’ve thought long and hard about sending your message. The winds have slowed, the light is perfect, and the skies are clear. You have two options.

  1. Notch your message, pull back the bow string, and fire that arrow straight into the apple above their head. Do no harm, but leave your mark on their mind, heart, and soul.
  2. Sheath your sword, return to your home, and throw your weapon in the fire, recasting it from a sword into a plowshare. Use your highly-enriched ire as fuel for something productive.

In writing him no new words about my hurt and anger, I chose the latter. I didn’t build the atomic bomb that went off at his feet, I had planted it there two years previous and gave him the launch codes. I deleted that insane list of his transgressions, as it was doing nothing but anchoring me to a hill I had no intention of living or dying on.

No, I’m not bitter about my mortal enemy, and you shouldn’t be with yours either. It’s a wasted opportunity. There’s another popsicle-stick idiom that says, “Living well is the best revenge.” That’s a bit too simplistic and short-sighted for me, so I once again turn to the words of Malcolm X:

“There is no better than adversity. Every defeat, every heartbreak, every loss, contains its own seed, its own lesson on how to improve your performance next time.”

As I said, in the same way my father likely doesn’t think of Warren Simms, it is exceptionally rare for John to cross my mind (I hadn’t thought of him for a very long time before sitting down to write this and I doubt he visits my attention tomorrow). But when he does slither from a crack in my brain, I take the tiniest bit of satisfaction in knowing that the rope only gets tighter around his neck with each passing day. He may not be as sentimental as I am, but the fallout will burn a hole in him the more he behaves in such a selfish manner as he did with me. In staying true to a moral and ethical code, his flashing memories will render me less a man and more a force of nature.

He has more money than I do, works in a career he loves, and will never have any shortage of young and naïve indentured servants to exploit. But it will fade. The artificial lights he uses to illuminate his life will flicker away, the bridges he burns to light his path will dim, and he will find himself alone and trembling in the dark.

In that valley, up his destitute mountain road, he may someday find himself at an impasse with a familiar tiger and its toothy grin. We will hug once again; to him our embrace will be embarrassing, a million vindicated teeth gnashing him like the selfish shellfish he knows he is, but to me it will feel like a reprieve from the heat of an indifferent universe, resting with an old friend under the shade of an apple tree with a newly broken branch.

Jesse Stewart is an American filmmaker, writer, and vindictiveness-vanquisher for Epocene Motion Picture Company.

Others in the ‘How To’ Series:

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Jesse Stewart
Jesse Stewart

Written by Jesse Stewart

Screenwriter, Film Director, and Chief Creative Officer for Epocene Motion Picture Company | Author

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