The doctor-patient relationship in The Wackness seems typical at first. It’s 1994 in New York, and a high school senior is enduring another fruitless session with his psychiatrist. The doctor says that he sees “no joy” when he looks at Luke. Luke detects misery wafting from Dr. Squires, too, which only validates the teen’s suspicion that the path to adulthood does not lead to happiness. “Tomorrow, I graduate,” Luke muses in a voice-over. “And then I go to my safety school. And then I get older. And then I die.” To both of them, there is no grass-is-always-greener scenario.

Unless that grass is packed in a bong. When Squires (Ben Kingsley) presses Luke (Josh Peck) to open up, and the kid finally blurts, “Dr. Squires, how much do you need?” he’s not talking about feelings. He’s talking about weed. Whether their sessions were cooked up to disguise Luke’s visits or the drugs serve as payment for sought-out therapy isn’t clear, but the arrangement blossoms into an odd friendship between two lonely dudes. Luke, floppy-banged and warm-eyed, deals dope in his Upper East Side neighborhood, drowns out his parents’ arguments with hip-hop, and interacts with other students only when they’re looking for the smokable kind of best bud. Squires, meanwhile, is a tastefully long-haired and goateed former hippie who doesn’t really see himself as a grown-up and is stunned to find himself in a cold marriage, numbing his melancholy with alcohol and the very prescriptions he refuses to give Luke, instead advising him to “embrace his pain.” Sex would help Luke, too, just as long as it’s not with Squires’ stepdaughter, Stephanie (Olivia Thirlby). “Getting laid is getting fixed, you know?” Squires advises. “Except for dogs.”

Writer-director Jonathan Levine’s film is a nostalgia piece about a recent but also rather different time, when old-schoolers like Luke refused to switch from cassettes to CDs and Giuliani was just beginning to clean up New York. (The former mayor is the movie’s main punching bag.) Grafittied placards mark the story’s progression throughout the summer, and hip-hop beats are constant, with artists such as the Notorious B.I.G., Nas, Raekwon, and A Tribe Called Quest filling the soundtrack. The tone is humid: It’s dark inside Squires’ wood-paneled office, but like most New Yorkers, Luke doesn’t spend a lot of time indoors. Instead, he’s sweatin’ his troubles outside, languidly pushing the Italian-ice cart that serves as his pot-delivery system through crowded streets and parks, his headphones providing the real chill.

Aside from the music and not-altogether-dated dialogue (“You’re mad outta my league,” Luke tells Stephanie), The Wackness is a classic story about first love and, more significantly, the struggles of the walking wounded who aren’t quite clinically depressed but can’t always get out of bed, either. Luke and Stephanie’s relationship is natural and engaging—Peck, from Nickelodeon’s Drake & Josh, and Thirlby, best known from Juno—are likably low-key and funny without seeming scripted. But the deeper and more interesting arc involves Squires. Kingsley, even with a dubious New York accent, makes Squires entertaining and tragic, out of touch with the demographic he believes he never left and the scene he imagines still exists. In one of the film’s best scenes, he takes Luke to one of his old hangouts, which is now not quite so happening. “The city isn’t the same,” Squires laments. “The drugs, the girls, the music—the fucking muuuusic,” he says, drawing out the last word with closed eyes and a heavy heart, and you feel his yearning. He finds a temporary distraction when some of Luke’s acquaintances show up, including a hippie princess played by Mary-Kate Olsen, who proceeds to crawl onto his lap. When the group finally gets thrown out, Squires yells, “They’re all 18!” Luke enlightens him that the drinking age has been 21 “since forever.” “Fucking Giuliani,” the doctor responds.

As both of them try to figure out what’s missing in their lives, the film gets a bit sitcom-like, but there’s enough weight to make gimmicks such as Squires helping Luke sell his wares forgivable. It doesn’t matter if you were a teenager in 1994, a flower child in the ’60s, or even a stoner in the here and now: The Wackness may touch on a few specific themes, but ultimately it explores the more universal question of how to deal.