Flying monkeys and enablers: the people in the middle

0:00The people in the middle

This episode is about a cast of characters who almost never think of themselves as part of the story. They are the friends who call to check on you and somehow relay everything back. The family member who says they just want everyone to get along. The mutual friend who messages out of nowhere to say he seems really sad, and have you thought about giving him another chance. They feel like neutral ground. They are not neutral ground. In the vocabulary of difficult relationships, these people are sometimes called flying monkeys — a phrase borrowed from The Wizard of Oz, where the witch never leaves her tower. She sends the monkeys.

I want to be careful with that phrase, because it sounds like an insult, and most of the people it describes are not villains. The term refers to anyone a controlling or high-conflict person recruits — usually without ever saying the word recruit — to do three jobs for them: gather information about you, carry messages to you, and apply pressure on you, all at one remove. The whole point of the arrangement is distance. Nothing ever comes from them directly. It comes through people you trust, people you cannot be angry with without looking unreasonable, people who genuinely believe they are helping.

And that is what makes this dynamic so disorienting. When the person who hurt you contacts you directly, you know what you are looking at. You have a category for it. But when your cousin calls to say she ran into him and he asked about you and he seemed so lost, your defenses do not engage, because your cousin is not the problem. Your cousin loves you. And yet, somehow, you hang up the phone knowing that he now knows where you work, and carrying a weight of guilt about his sadness that you did not choose to carry. The message arrived, the surveillance arrived, the pressure arrived — delivered by someone with clean hands.

I want to introduce the second term of this episode alongside the first, because they belong together. The flying monkey is the person being used. The enabler is the person who does not need to be used — the one who props the whole structure up on principle. The enabler is the parent who says but he's your husband, the friend who says there are two sides to everything, the relative who explains that he had a hard childhood, as though that were a reason you should absorb the consequences of it. Flying monkeys are recruited. Enablers volunteer. One is running an errand they do not understand. The other is defending an arrangement they do understand, because it costs them less than honesty would.

Here is the thing I want you to hold onto through this whole episode. In both cases, the mechanism runs on good intentions and ordinary human discomfort. Nobody wakes up and decides to become an instrument of someone else's control. They wake up and decide to be kind, to be fair, to not take sides, to keep the family together, to not make things awkward. The pattern does not need bad people. It needs good people who have not been told the whole story — or who have decided, somewhere below conscious thought, that your peace is a reasonable price for everyone else's comfort.

So this is an episode in two movements. First, we are going to name what is actually happening when these third parties appear — the shapes it takes, why it works, and why it keeps working even on intelligent, perceptive people. Then we are going to talk about what you can actually do: how to respond without briefing against yourself, how to sort the recruitable from the committed, and how to build a version of your social world that the pattern cannot reach. Because here is the good news buried in all of this. The flying monkey dynamic depends entirely on your silence, your politeness, and your isolation. All three of those are things you can change.

3:36The three jobs: eyes, mouth, and pressure

Let me break the dynamic down into its working parts, because once you can see the machinery, it loses most of its power. Every flying monkey interaction, no matter how warm or casual it feels, is performing at least one of three jobs. Sometimes all three in a single phone call.

The first job is information gathering. The eyes. This is the friend who asks how you are doing with unusual specificity. Where are you living now? Are you seeing anyone? How are you managing financially? It sounds like concern, and on the surface it is concern — the person asking may feel nothing but care. The question that matters is not how it feels to you. It is where the answers go. And you learn where the answers go when things you told exactly one person come back to you from the wrong direction, in the wrong mouth, wearing the wrong clothes. Information you shared in confidence returns as his knowledge of your life. That round trip is the tell. Once you have seen it even once, you know the pipeline exists, and you can decide what to put in it.

The second job is message carrying. The mouth. This is the classic errand, and it has a recognizable texture: the third party shows up carrying an emotional package that is not theirs. He just wants to apologize. He asked me to tell you he still loves you. He showed me the letter he wrote you and honestly it broke my heart. Notice what has happened here. Direct contact would let you judge the message, accept it, decline it, or ignore it. Routed through a third party, the message becomes a social obligation. Ignoring him is easy. Ignoring your kindhearted aunt is hard. The messenger has been chosen precisely because you cannot treat the message the way it deserves without also mistreating a person who does not deserve it. That entanglement is not an accident. It is the design.

The third job is pressure. The part that turns information and messages into leverage. This is where the enablers shine. Pressure sounds like: don't you think you're being a bit rigid? It sounds like: it takes two to tango. It sounds like: the children need their father, or: he comes to church every Sunday now, or: life is short. Every one of these sentences has the same structure. It takes a private harm, converts it into a social norm — be reasonable, be forgiving, be fair — and then positions you as the one violating the norm. The person who caused the damage is suddenly the status quo. You, by protecting yourself, are the disruption.

Now, why does this work so reliably, even on people who see through the person at the center of it? Three reasons. The first is triangulation: we are wired to take third parties as verification. When one person tells you something, you can dismiss it as their version. When three people tell you the same thing, it feels like consensus — even when all three are repeating the same original script from the same original source. The second reason is that the messengers carry social collateral. Every interaction with them risks a relationship you actually value, so you stay polite, you stay open, you keep explaining yourself — and everything you explain flows downstream. The third reason is simpler and sadder. After a relationship that made you doubt your own perception, a confident chorus of reasonable people is almost irresistible. You have been trained to outsource your judgment. The chorus is offering to hold it for you.

There is one more piece of machinery, and it is the one that does the deepest long-term damage: the smear campaign that usually runs underneath all of this. While the messengers are carrying his sadness to you, a parallel broadcast is carrying your reputation to everyone else — quietly, regretfully, with a tone of loving concern. I'm worried about her. She's not herself. She's been acting strangely since the breakup, and honestly I think she needs help. This is pre-briefing. It means that when you finally tell your side of the story — when you say, calmly and truthfully, what actually happened — the ground has already been salted. People have been prepared to hear your truth as a symptom. This is why so many people in this situation describe a slow, baffling social defrost: friends going quiet, invitations thinning out, a strange frostiness from people they have not even spoken to. Nothing was ever said to their face. That is what makes it deniable. And deniable is the operating condition of the entire system.

I want to pause here and say the thing that needs saying. If you are recognizing your own life in this description, the appropriate response is not paranoia. Not every concerned friend is a courier, and not every awkward family member is an agent. The difference, almost every time, is direction of flow. A genuine confidant takes information in and it stops with them. A courier takes information in and it moves. You do not have to accuse anyone. You just have to start noticing what travels.

8:44Enablers: the people who volunteer

Now let us talk about the harder half of this episode, because flying monkeys are, in a sense, an external problem — messages arriving from outside. Enablers are an internal one. These are the people inside your own life, often people you love, who stabilize the harmful arrangement. Not because anyone sent them. Because the arrangement, however much it costs you, is convenient for them.

Enabling has a bad reputation as a word — it sounds clinical and accusatory — so let me define it precisely. An enabler is someone who reduces the consequences of a harmful person's behavior, usually in the name of keeping the peace, and in doing so makes the behavior cheaper to continue. That is all it is. The mother-in-law who smooths every rupture so the couple never has to confront what caused it. The friend who says he's great when he's sober, as though the other days were weather. The sibling who tells you to stop bringing it up at family events, which means the family event stays comfortable and the truth becomes the thing that is not allowed in the room. Each individual act is small and defensible. The aggregate is a load-bearing wall.

Why do they do it? It helps to understand the motives, not because understanding obliges you to forgive, but because each motive has a different response. Some enablers are protecting a story. The family that has always presented itself as warm and functional cannot afford your account, because your account rewrites the family. So the pressure on you to be quiet is not really about him. It is about the mural everyone has agreed to keep painted. Some enablers are avoiding discomfort. Confrontation is expensive, and you are simply the cheaper person to pressure — you are the one who will absorb it, apologize, smooth it over, show up anyway. They have learned, correctly, that pushing on you works better than pushing on him. And some enablers are getting something. Access, money, status, grandchildren, a son-in-law who fixed their roof. The benefit does not have to be large. It just has to be theirs.

There is one more motive, and I want to treat it gently because it is the most common and the most human: the flattening instinct. There are two sides to every story. I'm sure it's more complicated than that. This is the enabler's favorite posture because it feels like wisdom and costs nothing. And sometimes it is true — most conflicts really do have two sides. But the flattening instinct treats all accounts as equivalent by default, and that is not neutrality. It is a decision. When one person is describing a pattern and the other person is describing the person describing a pattern — she's unstable, she's bitter, she's obsessed — those are not two equivalent sides. One is evidence about events. The other is an argument about the witness. Fair-minded people fall for this constantly, because hearing both sides is the habit of a fair mind. The question that cuts through it is not whose story sounds nicer. It is what each story is made of.

The hardest version of all this, the one that does the most damage, is the enabler who loves you. Because the enabler who is indifferent to you is easy to write off, but the one who genuinely loves you and still pressures you to go back, to be quiet, to keep the peace — that one scrambles your instruments. You know they love you. You can feel it. And so you conclude that their advice must be loving too. Here is the reframe that untangles it: love and understanding are separate quantities. Your mother can love you completely and understand almost nothing about what you are living through. Her love is real, and her advice is bad, and both of those can be true at once. You are allowed to keep the love and decline the guidance. That is not ingratitude. It is triage.

And because this episode insists on honesty in both directions, one more thing. Most of us, at some point, have been somebody's enabler. We have smoothed something over, told a friend to give him another chance because the dinner parties were easier when they were together, asked the wrong person to be flexible because they were the reasonable one. If that stings, let it sting usefully. The way out of having been an enabler is the same as the way out of being pressured by one: get curious about where your comfort is coming from, and what it is costing the person who is actually paying.

13:01Scripts for the people in the middle

Let us get practical, because this is where most advice about flying monkeys goes wrong. The usual guidance is to explain yourself — to sit the third party down, lay out the evidence, and win them over. Occasionally that works. Usually it backfires, for two reasons. First, every detail you give a courier is a detail in transit. Second, a person who has been pre-briefed for months does not evaluate your evidence the way a neutral judge does. They evaluate it the way we all evaluate information that contradicts a story we have already accepted: defensively. So the goal in these conversations is not to win. The goal is to control the flow — of information out, and pressure in — with as little drama as possible.

The foundational technique is the information diet. You do not owe anyone a briefing, and the single most effective thing you can do is to stop feeding the pipeline. This is not lying, and it is not being cold. It is choosing the size of your disclosures to match the demonstrated security of the channel. For people you are unsure about, there is a marvelous, all-purpose answer, and it is boring on purpose: I'm doing okay, thanks for asking. Work's busy. How are you? Notice what it does. It is warm. It is unrevealing. And it hands the conversational ball back. Delivered with genuine friendliness, it is almost impossible to object to, and it gives the pipeline nothing to carry. You will have to deliver it more than once, because couriers probe. Deliver it again, kindly, unchanged. The repetition is the message.

If you want to know whether someone is a courier, there is a gentle test, and it is the reverse of the diet. You give them a small, harmless, uniquely identifiable piece of information — something false in detail but innocent in every way, sometimes called a canary trap — and you wait to see if it comes back to you from another direction. If it does, you have learned something worth knowing, and it cost you nothing. Use this sparingly and without anger. You are not catching a spy. You are checking the plumbing.

When the messenger arrives carrying his package — the apology he wants passed on, the sadness he is performing — you need a script for declining delivery without attacking the messenger. Here is one that works, and it is short: I know you mean well, and I'm not going to discuss him. If he has something to say to me, he knows how to reach me, and I've asked him not to. I'd love to talk about literally anything else. Three moves: honor the intention, decline the errand, open a door to the actual relationship. If they persist — and committed messengers persist — you go shorter and flatter: I appreciate you. The answer is the same as last time. You do not need new sentences for a repeated question. New sentences are engagement, and engagement is the currency they are spending.

For the enablers — the people pressuring you directly — the script is different, because the relationship is closer and the stakes are different. With enablers, you can afford one real conversation, delivered once, calmly: I know you want us to work it out, and I know it comes from love. I'm not asking you to take sides. I'm asking you to trust that I'm making this decision from information you don't have, and I'm not going to debate it. If you can do that, I want you in my life. If you can't, I understand, but the topic is closed. Then — and this is the part everyone skips — you actually close the topic. Every time it reopens, you return to the close, kindly, without re-arguing the case. One deep conversation, then enforcement. Most people do the reverse: a hundred arguments, no enforcement.

And there is a distinction worth making explicit, because it determines where you spend your energy: the recruitable versus the committed. Some of the people in the middle are reachable. They got a one-sided story, they acted in good faith on bad information, and when they see the pattern — not your pain, the pattern — they quietly adjust. You will know them by this: when you decline to discuss him, they respect it. When you go boring, they stay warm. Those relationships are worth keeping and, often, worth deepening. And then there are the committed — the ones who, shown the boundary, treat it as a challenge. With them, the goal is not conversion. It is quiet, courteous distance. Not a dramatic cutoff, unless safety demands one. Just a slow reduction in access, until the pipeline runs dry.

17:33Rebuilding your side of the map

Everything so far has been defensive — managing the flow, declining the errands, enforcing the boundaries. I want to spend this last section on the other half of the work, because defense alone leaves you in a shrinking world, and the point of all of this is the opposite of a shrinking world.

The first rebuild is your roster. After a relationship like this, it is common to look around and realize how much of your social world was shared — his colleagues, couple friends, his family's holidays. That discovery can feel like one more loss stacked on all the others, and I will not pretend it is not a loss. But it is also a map of where to build. You are looking for people with one defining property: they are yours, not the relationship's. Old friends from before. People from your own interests, your own work, your own family where it is safe. And here is the specific instruction: invest in at least one or two people who have never met him, who carry no version of the story, who know you as a whole person rather than as half of a couple or a character in his account. Those relationships are not just comforting. They are recalibration. They remind your nervous system what it feels like to be believed by default.

The second rebuild is your reality base, and this one matters more the longer the campaign ran. A sustained smear-and-pressure environment does something specific to your judgment: it makes consensus feel like evidence. When everyone around you is calibrated to his story, you start to experience your own memory as the outlier, and that is a genuinely destabilizing feeling. The counterweight is external record and external perspective. Keep your own notes — dated, plain, unembellished — not to build a legal case but so that when someone tells you it wasn't that bad, you can check. And put at least one person in your life whose entire job is perspective: a therapist if that is available to you, a support group, one trusted friend who has explicitly agreed to be the person you check reality with. The question you are checking is never am I crazy. The question is: does this match what I wrote down at the time?

The third rebuild is your tolerance for other people's disappointment, and I mean this as a trainable skill, because it is one. Here is what nobody tells you about going boring, closing topics, and reducing access: it will disappoint people. The aunt will feel rebuffed. The family will find you distant. Mutual friends will call you private, guarded, changed. This is the tax on the new arrangement, and it is worth naming so it does not ambush you. Every system you exit — and the flying monkey network is a system — experiences your boundary as a malfunction, and sends you its complaints. Expect the complaints. Pre-decide your answer. Mine is: I hear you, and I'm doing what I need to do. Their disappointment is real, and it is also not an instruction. You can let people be disappointed in you. It is survivable. What is much harder to survive is the alternative — a life whose perimeter is set by whoever pressures hardest.

A word about timing, because people often ask when this gets easier. The pressure phase is usually front-loaded. The network is most active in the weeks and months after a separation, when the person at the center is most motivated and the story is freshest. If you hold your boundaries consistently — and consistently is the whole game, because every exception retrains everyone — the errands slow down. The couriers get bored. The enablers find other causes. Most people report a noticeable quieting within months, not years, and the quiet, when it comes, is disorienting in the best way. You will catch yourself bracing for pressure that does not arrive. Let yourself notice that. Noticing the absence of the siege is part of the recovery.

Let me leave you where I try to leave every episode — with the reframe that makes the work feel worth it. The flying monkey dynamic, and the enabling that holds it up, can only exist in the dark. It runs on your silence, your politeness, your reluctance to be the one who makes things awkward. Which means that every small act of clarity — every boring answer, every closed topic, every honestly named pattern — is not just self-protection. It is light. You are not cutting yourself off from people. You are finding out which of your relationships were real, and giving the real ones room to become the center of your life. That is not a smaller world. It is a truer one. And if tonight the pressure is heavy and the chorus sounds unanimous, write down one thing you know is true, in your own words, and keep it somewhere the chorus cannot reach. It will be there in the morning, and so will you.