When America’s in the mood to escape the unpleasant reality implied by statistics and facts—depressing at worst, dull at best—we tend to turn to the much sexier metric of TV milestones. What viewers consent to see on their screens often serves as convenient shorthand for what’s happening in the streets. The nation witnessed its first televised interracial kiss in 1968, at the height of the civil rights movement; in the ‘80s, broadcasters first put the boob in “boob tube,” a dubious victory for feminists; and “24,” the first torture-based procedural drama, aired its pilot episode just one month after 9/11, when the use of torture started to become procedural. The facts may be dull and depressing, but they’re no longer confined to the nightly news. Even TV’s not much of an escape these days.

Which is just one reason that the sweet, surrealist escapism of “High Maintenance” is a welcome addition to our airwaves. The series, which just finished its first season on HBO, is new to the small screen, but old to the smaller screen, where it began as a half-goofy, half-contemplative web series. The show is loosely centered on a nameless weed dealer, known only as the Guy (Ben Sinclair), as he bikes around New York, dropping into various lives and apartments and generally leaving before the smoke has cleared. Though the Guy possesses enough humor and charm to carry the series on his back—and a beard big and bushy (and Bushwickian) enough to swallow whole those who say otherwise—his clientele are the stars of the show. Each episode is devoted to a different customer: there’s a vegan couple who call up the Guy to dispose of a mouse humanely; a superhumanly fit artist with an odd outlook and an odder obsession with crystal catheterization; an asexual, amateur magician who regrets leaving his high-paying job at a porn magazine for a summer school gig, teaching bored and angry kids about Genghis Khan.

These characters lead diverse, depressing, whimsical lives, and are mainly unaware of the others’ existence, their stories neatly arranged in individual packaging. Though he’s not the star of the show, he acts as its unifying presence—the hub around which his customers rotate, like the spokes on his fixed gear. The earlier, web-based episodes were filled with loners (and their relationship equivalent, friendless couples), people who long for communion but usually settle for a dime bag. Still, for “High Maintenance,” lonerism has always been less the theme than the mood, a sort of precondition for all its antics. Because its characters want human connection so badly, they’re more likely to look for, and find it, in unexpected places, or people—say, their dealer.

Take “Helen,” for example, an episode about an excruciatingly agoraphobic recluse. Patrick lives with and cares for his sick mom, and spends most of his time obsessively styling his beard and ordering flannels online. The entirety of his social interactions occurs with the unsmiling couriers of his shirts or groceries, so it’s understandable that he would look forward to the Guy’s visits. This is only a little sad until the Guy actually shows up, and we see the two side by side—Patrick is clearly, and unsuccessfully, trying to emulate the Guy’s style. It’s a strange attempt at seduction that culminates with a half-hearted groping of the Guy’s ass (which he graciously ignores). The sad part is that he doesn’t even smoke, and just buys from the Guy to see him again. The man has a little box where he keeps the unused product, and, one assumes, his crushed dreams. But though Patrick’s feelings are unreciprocated, we still understand why he has them. When you can’t leave your house, your friends have to come to you—and the Guy’s the only person willing to step past the door, to enter Patrick’s life, if only briefly.

Other, Rogen-esque stoner comedies tend to use weed as a tool to expand small, meaningless stories into epic quests—think Harold and Kumar’s journey to a fast-food castle. But this expansion is usually more like bloating, the way one might feel after eating 27 White Castle burgers, all calories and no substance. “High Maintenance,” by comparison, uses the drug not to inflate but to magnify stories. That is, it knows the real drama comes less from intoxication itself than the reasons someone would call up the Guy in the first place—stress, chemo, family, boredom. The Guy gets to observe characters in moments of need, which reveal, in miniature, the entire shape of their existence. With this lens, he’s something of a modern flâneur, an urban ambler who, because he lacks a destination (and a 9-to-5) is privy to human moments that would otherwise get lost in the noise.

Still, the Guy is, like the flâneur, also an embodiment of the up and downsides of late capitalism. He’s able to observe people in their natural habitats—and to make a living at it—because he exploits a particularly modern type of alienation, in which most of a person’s human interaction occurs in a commercial setting, either at work or at the store. The Guy takes this trend a step further; he’s a salesman who’ll chill with you in your apartment while selling you a so-so substitute for a social life. The show’s format even thematizes this isolation—its brief episodes and changing cast mean that everyone gets the bare minimum of screen time, never enough for us to enter fully into their lives. This is the problem with the flâneur, and the Guy: they are by definition passive observers. As Baudelaire put it, the flâneur strives “to see the world, to be at the center of the world, and yet to remain hidden for the world,” which sounds about right for a man who bikes around New York, trying not to attract attention.

But the newer episodes have started to demand more of the Guy, and the viewer. For instance, “Selfie” explicitly challenges the Guy’s role as a passive observer, by giving him his first ever encounter with the forces of law and order. Rounding a corner on his way to a delivery, he comes upon police needlessly detaining two young black men. Other pedestrians have stopped to watch, and to film—we even get a shot from a cellphone camera, a homage to a newly ubiquitous, uniquely disturbing genre of viral images—to make sure this encounter doesn’t end, as they often do, violently. Normally, the Guy is the kind of guy who would join in and help, but his profession prohibits it: he can’t risk causing a stir while carrying contraband. He skirts by the police, eyes averted. It’s a remarkably uncomfortable moment, one that forces the viewer to question the Guy’s easy brand of optimism, based on the practice of people watching, the belief that anyone’s life, properly observed, is a wellspring of drama, humor, humanity. But there’s no uplifting story to be told about these two men, and no humor to be found in this encounter, which casts dozens of previous biking montages in a new light. While the Guy was so blissfully taking in the views, what less cheerful sights and stories were he, and we, missing?

But the show isn’t interested in easy answers to hard questions, preferring a quieter approach over loud polemics. When the Guy arrives at his destination, he meets his customer Anja, a writer at NYU, aspiring to be the next Joan Didion but only able to construct a social-media facsimile of her style and wit. She gets him to agree to an interview, and quickly, clumsily turns the discussion to race, in a feeble attempt to imitate her provocative idol. Still, she raises valid questions about bias and privilege: “Have you ever been arrested? Do you think that’s because you’re white?” We don’t get a satisfying answer to Anja’s questions, but then, maybe there isn’t one. The Guy does what he does, and isn’t any further outside the law than the millions of Americans now incarcerated for doing the same exact thing—just luckier, and funnier.

The show’s refusal to moralize, as Anja does, leaves open other, unexpected routes to a just resolution. The second half of the episode is a loosely constructed series of meta gags, revolving around a fake TV pilot featuring a bearded dealer-on-wheels named “Guy.” It’s a wry, meta-moment in an episode full of them—for one, the show-within-the-show markets itself as a “hilarious hipster comedy,” parodying the quirky plot conceit of “High Maintenance” as little more than a desperate grab for a certain demographic. But “High Maintenance” goes beyond self-deprecation to position itself in a wider television landscape, staking out its own original territory while acknowledging other, prior claims to the city: there’s a moment where the Guy gets held up on a delivery, forced to wait on the sidewalk while “Girls” finishes shooting a scene. What’s more, the Guy is delivering to none other than Hannibal Buress, who passes the time by “rewatching some of my epic ‘Broad City’ performances,” a nod to another former web-series set in New York, with similar habits and a similarly weird sensibility. All this would be fairly unoriginal—though still funny—were it not for the first half of the episode, which seems to weigh on the Guy’s conscience. He ends up agreeing to testify that the TV pilot plagiarized his own life (as well as that of a less-than-sympathetic homeless woman), leading to a hilarious scene of him describing his profession while trying not to admit to any illegal activities.

It’s a small victory for justice, especially compared to the Guy’s earlier refusal to confront the police, a defeat by forfeit. Still, it’s a new direction for the show, one that finds it not withdrawing from the world, like the loners its earlier episodes tended to depict, but engaging with it. The series, in short, has left the web for good, and begun to look and feel like a legitimate TV show, complete with recurring cast, entrancing cinematography, and a perfectly curated psychedelic soundtrack. But it’s also starting to behave like one, acting as a barometer for our national politics. The show remains interested in the small-scale stories of individual smokers—normal people with an increasingly normal habit—even as it has become newly attuned to sensitive and pressing questions about the injustice and bias of our drug laws. Fitting, given that five states will be voting on recreational legalization in a couple weeks. In this sense, “High Maintenance” is less easy escapism than a return to reality. Senses heightened, not dulled, by his drug of choice, the Guy is ready to join a national conversation—right after he takes this hit.