IF YOU’VE EVER made the choice not to watch Nathan for You, there is a good chance you did so because it seems kind of exploitative. Without context, its premise sounds like a tastelessly classist prank show or some Sacha Baron Cohen thing: A guy with camera crew shows up to “help” struggling small business owners, but instead puts them through all kinds of ridiculous and uncomfortable ordeals that only ever help them incidentally, if at all. If you do not enjoy watching unsuspecting people get made fun of for sport, you could be forgiven for thinking Nathan for You is not your version of a good time.

You could also be mistaken. This past October, the A.V. Club published a delightful interview between Fielder and editor John Teti’s mother Bonnie, who starts out hating the show and leaves the conversation a convert. Here’s Fielder response to her accusation that the show makes fools of its participants:

Some people view the show that way, and that’s totally valid, but personally, I don’t find the people involved in the show, for the most part, to be foolish. […] The situations and the uncomfortable moments in the show […] are designed to bring out a side of the other person that I find very charming and endearing. […] A lot of people come into a situation, especially when they’re being filmed, where they have a certain idea of how they want to present themselves. And that part is usually the least interesting part of them because it’s very controlled, and I’m trying to show who they really are in some little way — with very low stakes.

This focus on human nature has become the Nathan for You fan’s go-to defense; every review of the show and profile of its creator makes sure to mention its empathy, its “secret humanity.” It may look like a prank show from a distance, the argument goes, but at its core is kindness — a deep-seated (if weirdly articulated) affection for people and their quirks.

This reading posits Nathan for You as a comedic inversion of a familiar reality show structure. If most corral their characters into rigid narrative arcs, only giving us small glimpses of their participants’ truest and weirdest traits, Nathan for You goes through the looking-glass, deriving its structure and comedy from its attempts to bring those quirks and eccentricities to the surface. Rather than ferrying us past the strange, unique, and awkward moments that can arise in the course of everyday human interactions, each episode’s narrative functions as a device to move us (and Nathan) from one to the next.

In one sense, this all checks out. Every episode of Nathan for You is deliberately structured so that no matter what happens, Nathan himself is always the punchline. His subjects can go through on-camera exorcisms or admit to drinking their grandchildren’s urine, but no matter what, the joke is always ultimately on him — his seemingly pathological awkwardness, his failure to help the businesses he’s brought in to assist, and his failure to recognize his failures for what they are. No matter what anyone else does, they are always doing it in reaction to Nathan. This is the show’s failsafe, and the fact that it’s invoked in every single one of its segments speaks to a kindness that’s not just philosophical but practical, and built-in.

Plus, by all accounts most of the business owners featured on the show aren’t bitter about their experience (which, as Molly Lambert notes, is more than you can say for most actual business-based reality shows), and discomfort is usually the worst thing anyone experiences in the course of an episode. No one gets hurt, no one loses money (except customers who get pulled into Nathan’s schemes, which tend to be pretty low-impact), and nobody’s ever really forced to do anything they don’t want to do.

But that modifier is important. Much of the show is predicated on the way Nathan gets people to agree to things they’re clearly, achingly uncomfortable with. Nathan for You might not be designed to punish its participants, but it absolutely takes advantage of their politeness, their credulity, their confusion, and their desire to be on TV. The whole show depends on Fielder’s ability to work the inherent imbalance of power between Nathan and his subjects (which is itself multilayered — yes, he gets to play a character while everyone else on the show is stuck being themselves, but there’s also the plain fact that he’s a white guy, and many of the business owners he shows up to “help” are not). Everything about Nathan — from his business-casual-bland outfits to his camera crew to his predilection for getting people to sign elaborate contracts — is designed to give him an aura of authority, and the show’s funniest moments come from watching people try to reorient themselves as that aura burns off.

Your reaction to the way the show constantly positions Nathan as its ultimate punchline is a good litmus test for your ability to enjoy the whole thing. If you are willing to see the show’s failsafe as a gesture of kindness toward its other subjects, then you’ll probably be able to sit through an episode without turning it off out of discomfort. But if there’s something about that that rings false to you — like the kind of self-effacing joke that’s never really on its teller — then you might not be the audience Fielder is looking for. There’s a moment in that A.V. Club interview where Teti tells him she initially found Nathan “superior,” and he can’t really say whether she’s right or wrong. It’s a harsh reading, but not entirely incorrect; there’s a lot of terrain between laughing at people and laughing with them. The show might not be exploitative or explicitly mean to its subjects, but they are still its grist, and ultimately, your ability to stomach that fact is what will determine whether Nathan for You is, in fact, for you.

As a sidenote, I don’t think it’s a coincidence that many of the people I know who rep hardest for the show are straight white men — the demographic least familiar with the experience of having its social boundaries violated on a daily basis, as a matter of course — nor is it a coincidence that most of my friends who can’t really get into the show are not. For these people, the problem with Nathan for You isn’t necessarily with Fielder, who’s clearly possessed of an extremely functional sense of empathy (you have to be preternaturally good at reading people to pilot a character who sucks at it as thoroughly as Nathan does). It’s more about the difference between understanding the joke and actually finding it funny — something that might be harder to do if you already find yourself facing a chorus of real-world Nathans every time you log onto the internet, or leave your home.

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One of Nathan for You’s most reliable tropes is Nathan’s obsession with loopholes and the letter of the law, which manifests equally in his business schemes and conversations: he’s obsessed with contracts, doesn’t really understand how euphemisms work, and builds most of his plans around technicalities. (The entire existence of “Dumb Starbucks,” for example, is predicated on a real thing called “parody law.”) Per Fielder himself:

… from what I gauge is the culture on Wall Street these days, [the mentality] is, the only way to make money is to find a loophole that’s technically legal but one step ahead of anything anyone else has thought about. They don’t really think about how it’s affecting the world or the moral or ethical issues with it. […] Part of me tries to take on that mentality a little bit. To put on the blinders to any sort of consequences outside of that.

This obsession with loopholes is one of a few things about Nathan’s personality that serve the dual function of highlighting an ugly truth about something like capitalism while also drawing it all the way down to the level of conversation, of gesture. But if many of his schemes balance on his eagerness to find a small technicality and exploit it, Season 3’s climactic finale takes things to an entirely new level. In ”The Hero,” Nathan and his crew take to the “food courts, coffee shops, gas stations, and comic book stores” of LA looking for people who might want to be on a reality show that offers them a “life makeover.” They find Corey Calderwood, a part-time arcade attendant who lives with his parents in Ventura, and seems cautiously excited about this mysterious chance to change his life.

On another show, a life makeover would see Corey going through a course of self-improvement, therapy, or dramatic change on his own, but in Nathan for You-world, it means that Nathan studies his voice and mannerisms, commissions a Hollywood makeup artist to create a 3D prosthetic mask of his face, takes away his phone and I.D., and then sends him, blindfolded, to a trailer in the middle of the desert where he stays for weeks as Nathan systematically takes over his life. The whole scheme culminates in a dramatic stunt where Nathan, in full Corey-mask and bodysuit, performs a tightrope walk (for charity!) between two buildings in downtown LA, switching places with an incredibly confused Corey, who’s just been flown back in from the desert, at the end.

At one point in the episode, Nathan sets up a fake OKCupid profile for Corey and embarks on a date as him, mask and all, with a woman named Jasmine (who seems lovely, who I really hope got something nice out of this whole thing). Their night goes well, and at the end of it Nathan asks if he can kiss her — but when she agrees, he explains that he meant next week, right after he’s completed his heroic tightrope walk. Jasmine is game, so later, right before the walk, as Nathan is giving an incredibly confused Corey a harried run-down of the whole situation, he opens a binder to a picture of her. “This is your girlfriend,” he says. “She’s already consented to kissing you.”

Corey looks appropriately concerned, but once Fielder pulls off the stunt and they switch places, he kisses Jasmine three separate times in front of the cheering crowd, before delivering a speech Nathan’s written about how he couldn’t have done any of this without her. (I had to watch the episode three times before I could actually look as a wincing Corey reads the line, “Jasmine, I love you,” into a microphone while she stands behind him and whispers “…what?”)

The rule of Nathan-as-ultimate-punchline still applies here. Everything in the episode is bounded by his complete misunderstanding of (or deliberate disregard for) emotion and nuance, how he prioritizes technicality over the way any of this stuff might make Corey (or Corey’s family, or Jasmine) feel. But a more complicated source of humor — the part of the episode that’s funniest, but least like a joke — is in watching how fast Corey relaxes into the whole scheme against what’s clearly his better judgment. Just before he goes to walk the wire, Nathan asks with hyper-dramatic reality-show flair if Corey is “ready to be a hero”; it’s amazing and horrible to watch him fumble for any kind of logic or lifeline. “Uh,” he falters, “I guess we got it all set up, so we kinda… kinda gotta do it now…”

But in the end, Corey goes along with it; he gives the speech, kisses the girl, waves to the crowd, talks to the news crews assembled below. In the elevator on the way down from the roof, there’s even a weirdly touching moment where he nudges Jasmine shyly with his shoulder, just a kid on the most bizarre first date of all time. Once he’s reached the ground he walks into the crowd holding her hand, nodding as people pat him on the back and offer their congratulations.

If your enjoyment of Nathan for You is at all contingent on its being morally sound — if you’re the kind of person who notices and cares about the difference between this show and, say, Punk’d — then there’s a way to talk yourself into not feeling weird about any of this, but it’ll cost you. This is one of the show’s most complex tricks. Technically, Corey agrees to be on a reality show that will give him a “life makeover,” and technically, that’s what he gets, even if it isn’t quite what he was expecting. Technically, Jasmine seems happy to kiss him, and technically she doesn’t know that Nathan and Corey are two different people at all when she does. The crowd sees what they showed up to see (a guy on a tightrope for some reason) and in a sense, everyone gets what they came for.

But watching the show like this means you have to mute your sense of empathy. You have to ignore the obvious flickers of hesitation that cross Corey’s face every time Nathan asks if he’s ready for what comes next. You have to ignore the fact that Fielder and his crew spent months combing LA for sad, vulnerable people who don’t like their lives, and then flew one of them out to the middle of the desert where he lived for two whole weeks in isolation, only to come back and be placed in the middle of an incomprehensible, chaotic situation that pressured him into lying to a lot of people in a lot of small, weird ways. You have to ignore the fact that — Nathan’s flawless impersonation notwithstanding — Jasmine said yes to kissing one guy and then got tricked into kissing a different one.

In other words, if you want to like the show without ever feeling weird about what it means to like it, you have to do so on a technicality — the same kind Nathan is always exploiting at the expense of his ability to be a good person. It’s the low-stakes moral equivalent of going through a two-foot-tall door to get to a room that leads to another room with an alligator in it, all just so you can buy a $1 TV. You could, theoretically, maneuver your way through the course, but at some point you’ll have to face how hard you’re working just to ignore your better judgment.

There’s a particular kind of laughter this show draws out of you, even when you’re watching it alone — involuntary, full-body, forceful. Its most successful moments are incredibly funny, but they’re also shot through with pathos, loneliness, longing and discomfort, and that laughter is what your body does when your brain is dealing with the dissonance of a moment that contains all of these feelings at once. The most emotionally honest way to watch Nathan for You is also the least comfortable: you have to dive headfirst into the unease of the whole thing. You have to go through the show instead of just watch it.

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Awkwardness might be Nathan for You’s most talked-about aspect, but the show also packs more experimentation, invention, building, and testing into its 22-minute frame than anything else on TV, including reality shows whose entire focus is building and testing stuff. Some of the show’s most delightful moments come from just seeing the sheer amount of work Fielder and his crew put into pursuing an idea; the pleasure of watching him invent a problem, propose a solution, and then chase it way beyond the limits of common sense is pretty unique (and surprisingly innocent). It’s the comedic-reality-show equivalent of watching someone knock down a meticulously arranged chain of dominoes; a downhill feeling, visceral, and a distinct relief from the intestine-wringing discomfort of watching Nathan talk to people.

A friend of mine calls Nathan’s approach to problem-solving “the suspension of logic in favor of logic.” Every one of his ideas has a rock-solid internal consistency, and Fielder (with the help of a clearly dedicated crew) employs such an impressive procedural rigor in following them through that it becomes easy to forget that most of his schemes don’t really make sense. It would, for example, be more than enough to watch the unrelenting care and attention to detail with which Nathan’s crew constructs a $20,000 “sex box” (a chamber that parents can lock their kids inside when they want to bone down on vacation, replete with six-inches of soundproof batting, cork lining, a submarine-grade breathing system and a rubber base “to eliminate vibrations”) for a perplexed hotel owner who doesn’t really want it in the first place — but because Nathan leaves no stone unturned, he has to test it, too. For this he hires a child actor and two porn stars, locking the kid in the box while the adults have incredibly loud sex just a few feet away. The child’s parents try at first to stay in the room in the name of ensuring their son’s safety, but once the performers start calling each other by the parents’ names (Nathan’s way of making the scenario “more realistic”) they high-tail it outside, waiting in the hallway in a silence so intense it’s practically visible. Once the couple finishes, Nathan opens the lid to check that the kid hasn’t heard anything, and then he closes and locks it again, bringing in five more performers for an orgy, just to be sure the box can stand up to anything.

If nothing else, Nathan for You is a really, really well-edited show. The way all this process and preparation gets played against the slow, aching burn of Nathan’s one-on-one interactions gives the whole thing a cadence that’s as unique as it is satisfying; you’re watching someone invent a new kind of joke and the language that’s required to tell it at the same time. All these twists and tangents get stitched into a swift-moving structure that pulls you through Nathan’s schemes the same way good enjambment directs you through a poem, or a PVC tunnel guides a pig through a trout pond.

As the series progresses and Fielder and his crew become more comfortable with its rhythms, the show’s main structural strength becomes the fact that it doesn’t really have a fixed form at all. By the third season things still operate, more or less, out of the Nathan-as-fixer premise, but each episode bends a little differently to accommodate the characters he meets and the roadblocks he encounters. This flexibility is a structural echo of Fielder’s own personal skills as an improviser, and the overall effect is an experience that feels less like watching a half-hour of Comedy Central programming and more like taking a quick trip through Nathan’s own mind.

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Fielder is a fan of magic. There’s this lovely moment in a 2014 New York Times Magazine profile where he describes the appeal of a good trick:

There are times when you find someone who does something so new that you’re not thinking about the moves anymore […] You’re just blown away, and you’ve got no idea what the hell just happened.

Fielder, his character and show, all share an obsession with the possibilities of immersion and absorption. Each of Nathan for You’s schemes is designed to work this way; an arrangement of technical maneuvers that resolve, alchemically, into a completely unique moment. And Fielder’s steadfast commitment to being Nathan (which isn’t just philosophical but physical — when Nathan spends five hours in a car with a P.I. on a stakeout, or trains for months to pull off a stunt, Fielder does too) is its own kind of disappearing act. But over the course of season three, this fixation turns from a trope into something more like a tidal wave.

In the first two seasons, the central feature of Nathan’s personality is his misfiring desire to get someone — anyone — to be friends with him. Sometimes this manifests in ill-conceived attempts to make himself more likable (like the one where he gets a handful of strangers to follow him around in a box truck and focus-group his personality in real time), but mostly he just ends segments by asking the business owner he’s just failed to help if they want to hang out with him later, forcing them to scramble for the right way to say no when there is none.

But in season three, Nathan starts going undercover a lot. All of a sudden most of his schemes involve dressing up; he disguises himself, variously, as a Hot Topic employee, a bro, a drunk, that same drunk in a Peter Pan costume, and a biker, all with varying degrees of success. When he’s not impersonating someone else, he’s performing a surrealist inversion; in episodes like “The Movement” and “Smokers Allowed,” he builds fictional worlds so overwhelming and elaborate that they swallow the fabric of reality, and then forces everyone around him to act according to their rules.

All of this is what makes “The Hero” a perfectly reasonable next step in Nathan-logic, even if, for most people, the connection between “making yourself more fun to hang out with” and “training for seven months to walk a tightrope while wearing a custom-made bodysuit” isn’t exactly intuitive.

In that episode, after his date with Jasmine ends, Nathan decides to stick around at the bar. We see footage of him having a night on the town in Corey-drag, and for the first time in the entire series, it seems like he’s having a truly good time — he laughs, dances, buys rounds of drinks for strangers, and takes photos with them. He might be wearing a prosthetic mask that took four hours to put on, but he looks comfortable. He looks happy.

Over all of this, he delivers a heart-piercing monologue:

I found myself strangely surprised by my own confidence. There was something about being in another person’s skin that made all my social anxiety vanish. I was able to charm complete strangers. It was a side of me I had never seen before. It was nice, for once, to have a night away from all my insecurities, and as it came to an end, I actually felt a bit sad knowing that I’d soon have to go back to being me.

There’s a parallel moment later, after he successfully walks the wire for the first time, where Nathan pauses for a few seconds to bask in his success — and then steps back on. He crosses the wire again and again and again, walking it five times in total while the crowd below keeps cheering for him. In voice-over, he tells us what we already know: “I wasn’t ready to stop being Corey just yet.”

One of social anxiety’s cruelest side effects is how thoroughly and instantly it turns you into a narcissist. A lot of people think you need an excess of self-regard to be self-obsessed, but as any experienced overthinker will tell you, all it really takes to become completely absorbed in your own inner world is the staticky rush of adrenaline that comes of truly fucking up a conversation. In these moments, the full force of your attention swivels inward; everything else in the world dissolves until all you can see is you, your flaws and inadequacies and failures lit up like a marquee.

This kind of anxiety is one part of a more complex trap. You can’t really be alive without wanting to be loved, and you can’t really love someone else without empathy, and you can’t really be empathetic without figuring out some practical way to mediate the messy, overwhelming and completely legitimate fear that maybe no one in the world will ever love you. If you want to connect with other people, you have to learn to drag your attention away from yourself and focus it on someone else — but the sheer force of your desire for that kind of connection, if left unchecked, has the power to swallow your attention and erase your capacity for empathy before you ever get the chance to try.

Often we describe people who don’t know how to hide their desire for love and approval as desperate or pathetic. That revulsion has a lot to do with how close to home it hits to see someone grasping for love with the same desperation we’ve painstakingly learned to conceal. This is why everything that’s funny about Nathan’s cluelessness is also frustrating and kind of heartbreaking — why it feels the way it does to watch him “help” someone become a hero by banishing them from their own life, or build an entire The Bachelor-style reality show around himself to cure his anxiety with women, or trick a Craigslist stranger into giving him blood and urine samples so he can scientifically prove (“once and for all”) that he’s fun to hang out with, or get a young woman in a play he’s directing to say “I love you” to him over and over, in character, until actual tears spring to his eyes. Nathan’s desire to connect is so messy and sprawling, and the ways he grasps for that connection so convoluted and backwards, that the closest he can ever come to getting what he wants is when he can convince people to fake it for the show.

All of this is why his turn from simply wanting people to hang out with him in the first two seasons to wanting to become someone else entirely in the third makes a complicated kind of sense. In terms of pure outcome, being loved for who you are is pretty much the same thing as becoming a whole new person. In both cases you’re allowed, for a moment, some reprieve from the exhausting task of being yourself; in the former because you’re finally safe, and in the latter because you’re finally free. When Nathan steps into the role of Corey — whether he’s buying shots for his new friends at the bar or walking the wire for the crowd — he gets to collect the love and acceptance he craves on a technicality, the only way he knows how.

But in the end, you can’t force or fake an escape from yourself; you can’t trick anyone into loving you through a loophole, and you can’t really become someone else, no matter how elaborate your disguise might be. The only real way to untangle yourself from yourself, to quiet the dull roar of desire and fear and longing in the background of your thoughts and actions, is to broker some truce with your attention that lets you focus it on the people around you instead.

Knowing all of this is one thing, but actually caring about others — practically, actively, consistently — is one of the hardest things in the world to do. There are a million ways to fail at it, each more cringe-inducing to watch (or recall) than the next. This is the fact on which Nathan for You’s improbable, uncomfortable magic depends; the thing that makes this show harder and better and worse to watch than anything else on TV. Its brightest laughs may come from the awkward moments Nathan creates by misplacing his attention, but its power comes from the way it feels to watch him act out that mistake again and again, with everyone he meets.

In other words, the show works the same way a person does: complex and contradictory, with moral friction at its core, and a huge mess of crossed wires between its intentions and its actions. If the disappointment of most reality TV shows is in how they take the trappings of truth and paste them together into something empty and easy, then Nathan for You works the other way around: by taking a comedy and turning it into a reality show, in the truest, least comfortable sense of the word.

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Emma Healey is the author of Begin with the End in Mind (Arbeiter Ring Publishing, 2012). She lives in Toronto.