High Maintenance follows a Brooklyn pot dealer, The Guy, as he delivers to clients with neuroses as diverse as the city. Heis an everyman pot dealer who makes cameo appearances in the lives of various New Yorker City residents, providing them with weed and getting a glimpse at their daily routines and how they light things up.
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When Rocky hears a sneeze through his apartment wall, he falls down a shame spiral, reliving embarrassing moments. An attention-seeking A.J. fails to make plans for Halloween—until an emergency text from an ex-friend, Francis, evolves into an unexpected night with Francis' assistant, Cheyenne.
The Guy delivers to ASL interpreter Jordan, who lands in an uncomfortable situation on a job at a high-profile photo shoot. After Victor notices that his partner, Ellen, has a new habit, a secret blows up amid already simmering tensions in their relationship.
Two former friends share an awkward ride, and The Guy has an interesting ride-share experience of his own. Meanwhile, when a patient asks her out on a date, dental hygienist, mother and caretaker Nora wonders if she can put her needs first for once.
Shy sneaker head Alvin spends most of his time to himself, but gets a new challenge when he spends the day with his cousin. The Guy attends a dinner party hosted by an old friend, Jackson, and as the night progresses, realizes he might be out of his element.
Two sisters clean out their childhood home after the untimely death of their mother. The Guy delivers to a bickering couple renegotiating their relationship. And a new mother hosts her teenage cousin from out of town.
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When The Guy and his eclectic jury duty group head to a karaoke bar to mark the end of their civic service, Keesha and Roman, the youngest members of the crew, run into trouble. While exploring a side hustle with her friend Violet, Freddie encounters someone from her past.
The Guy, with new friend "Fomo" in tow, delivers to Matthew, a man looking for a connection who hires a new-to-the-business escort for the night. After bonding on set with a familiar face, intimacy coordinator Kym learns a surprising fact about her new love interest that threatens to derail their romance just as it's beginning.
The Guy finds a lost canine. A new reporter at This American Life, Yara pitches a story about her parents' marriage and inadvertently strains her own relationship when her boyfriend Owen visits for their anniversary weekend. A singing telegram in a bad mood looks for some relief while crisscrossing the city on a crazed workday.
Leonard, an acting teacher, contemplates moving back to New York. The Guy connects with old high-school friends Sarah and Brian, who are visiting the city under difficult circumstances.
A couple adjusts to life with a special delivery; The Guy hangs with a young nanny.