This first feature by writer/co-director/star Mark Blane is a “Welcome to New York” tale for the pampered, overprescribed, millennial archetype. A gay man-child who lives in his mother’s basement somewhere in Indiana makes up a lie to her (Patricia Richardson from TV’s Home Improvement) that he got a job as a receptionist at a fancy New York City art gallery, and she drives him cross-country and drops him smack in the middle of Soho.

Mark has no place to live, no job, and he’s out on the streets all because he wants his mom to think he has a job in Manhattan. Luckily he has a friend in the city, Greg (John Duff), Mark’s former college roommate who lives in the Bedford-Stuyvesant neighborhood of Brooklyn. Well, actually it’s Noah-Gregg, with two G’s because he’s Brooklynized himself. Mark finds a room in Noah-Gregg’s collective apartment where everyone is “killing it” at their very professional jobs. They eat only gourmet food that Mark has never experienced before and speak only in the social media lingo du jour.

Mark takes a part-time job babysitting Milo (Joseph Seuffert), a sensitive and artistic little boy, very much like Mark himself. Mark barely functions in the adult world, but when he’s with Milo he has a sweet release from responsibilities, as the little boy is the only person in the city who really gets him. This is much to the chagrin of Milo’s parents, especially his mother (Jeanine Serralles), who, despite her son’s love of his new babysitter, would much rather he spend time with someone who can provide more structured care for him.

For indie/queer film buffs out there, Cubby will remind them of Mike White’s cult classic from 2000, Chuck and Buck, also about an adult-aged gay man who lives with his mother and then is suddenly transplanted to a big city, in this case Los Angeles. Mark, like Buck before him, isn’t incapable. He went to college and displays an impressively elevated vocabulary. He just suffers from arrested development, presumably from moving back in with his mother right after college and not having the will power to figure out his own path in the workaday world.

There is, of course, the fact that Mark is gay. It’s not hard to imagine that back in Indiana he didn’t have much exposure to gay culture. What he knows about it is from porn, and he re-creates in his artwork Tom of Finland–esque sketches of men in leather having sex. Shortly after arriving in New York, Mark sees a group of men engaging in BDSM (it’s unclear if this first instance is a hallucination), and one of the men in particular catches his eye, a silver-fox man dressed from head to toe in leather (Christian Patrick). Later, when on a hallucinogenic cupcake trip, Mark imagines seeing this character again in a men’s room. The man, whom Mark dubs Leather-Man, becomes his personal superhero and father figure.

This film nails the culture shock of having moved from the Midwest to New York City, or any major city for that matter. I cracked up every time Mark displayed a clueless look whenever he saw what someone was eating or looked absolutely lost at some of his roommates’ pseudo-intellectual discussions. Then there’s the annoyance of being bombarded with gay culture’s idealization of sculpted bodies, such as Mark’s roommate, Noah-Gregg, who even around his own home flaunts his physique by donning spaghetti strap tank tops and crop tops. Blane himself is less conventional looking, having an oblong face, a crooked mustache, jowls, and buckteeth. So the body positivity going on here is commendable.

All in all, Cubby may not be everyone’s cup of tea, but it certainly will strike a chord with a lot of us weirdoes who’ve striven to find exactly where in the world we fit in.