What Your Weed Delivery Guy Thinks About You (I Asked)

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If you’ve never seen High Maintenance, it’s a show in which the only recurring character is “The Guy,” a.k.a. a nameless weed dealer who delivers his product via bicycle to clients all across New York City. It began as a web series and then went viral, eventually landing on HBO where it just began season three. The appeal? The Guy, and the window he provides into all different kinds of lives across the city.

The Guy of High Maintenance may be fictional, but his job? Very real. The IRL guy is gender non-specific and typically shows up with a briefcase of a whole bunch of goodies. But do clients know any more about the guy than that? Well, you’re about to. Below, an as-told-to interview with one such “guy” who divulges everything from how they get around to who they’ve delivered to. You might wanna spark an L for this one. Or just pop a CBD gummy.

I moved to New York two years ago and was working a part-time job while pursuing an acting career when I quickly realized how hard it is to live here. One of my friend’s girlfriends worked for the service and had mentioned that the hours are really great, that it pays incredibly well and that you can create your own schedule. I looked into it and yeah, it is a great job — despite riding a bike for 10 hours a day. People might think that we have a different way of traveling in bad weather but we don’t. I was even expected to learn how to fix a bike.

The organization is rather large and so much more structured than you would think. It runs like a legal business and has a hierarchy of power, but it’s also a rather friendly community. There’s not necessarily a human resources department but there are people that you are supposed to reach out to if you have any kind of issues. I think that even goes to show how people who do participate in a business like this are not just burnouts. They’re not amateurs. These are also people who are doing other things — some people are artists, some work in computer science. Some use this as a part-time gig three times a month to make some extra cash.

Everything we sell is THC weed-based. Nothing different, nothing harder — people will ask that all time. We do not engage with other substances at all. Since weed has become legal in more and more states we are keeping up with really interesting products. Cartridges, different kinds of edibles, things like that.

I notice that when I’m delivering to families, it’s a very casual thing. There are parents that live in the West Village or in Greenpoint or whatever, ordering weed at one in the afternoon after they give their toddlers lunch. I deliver to young adults when their parents are around. All of those people are white for sure. I think they see how much more accessible weed has become within our society but might not understand why or how — on the backs of Black and brown people. Now this thing that has been used as a way to incarcerate people of color is now a highly demanded thing that affluent white people love.

I’ve noticed that a lot of people will order the weed for their parents or grandparents. Kids become the middle men because weed’s been systematically framed in a way that older people can’t comfortably engage in purchasing it. Noticing the relationship between older generations and weed now has been one of the most shocking things because they judge it, but then secretly get it from their kids or from us.

One time I actually delivered to someone I went to high school in Maryland with — that was very awkward.

There’s this really funny older white guy, he must be in his 70s. He has a really nice house, a cute little Bichon dog and these nerdy glasses. I feel like he’s some kind of writer. He never remembers me. Every time I go over there he likes to look at the weed and sniff it.

“Oh man, back in the day we would just order things off the street from these sketchy guys. We would have no idea what it was. Usually it would just be oregano. This is something,” he’ll say.

He tells me this story every time I’m there and I just kind of act surprised like I never heard it before. And then every time before I leave he goes, “Oh, what are you guys calling it these days?”

“Usually bud or flower,” I tell him. And then he’ll say it to himself before going, “Okay. Cool, cool.” I think it’s kind of his way of accessing and connecting to younger generations.

I also deliver to this college kid on the Upper West Side. Every time I go up there his mom’s home. I’ll come in, she’ll think I’m just a friend, but eventually she’ll be like, “Oh, is that the weed guy? It stinks in here!” Then a little later she’ll be like, “Well, I got cookies once you’re high.” It’s a very playful thing.

I’ve delivered to amazing penthouses, beautiful apartments, cool people — and a celebrity once. An actor on a television show who was really sweet and so curious about the business and the lifestyle of being a dealer. I’ve had people hit on me before. I’ve had people give me their phone numbers. I’ve also had people who call when they’re really drunk and cry to me. One time I actually delivered to someone I went to high school in Maryland with — that was very awkward.

Protocol says don’t smoke with the customers but there is this sweet older woman who has MS and her condition is constantly fluctuating — I will often smoke with her. We talk about life and she gives me great advice. That’s another beautiful thing about this job — when you deliver to people, you get this sense that you are helping them a little.

It surprises me oftentimes how cool people are when I put on the proverbial weed delivery guy hat. There’s this whole new world that opens up — a whole new relationship between two people you would never, ever think would interact with one another.

Photos by David Russell/©HBO/courtesy Everett Collection.

Emma Bracy

Emma is the Associate Editor at Man Repeller.

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