High Maintenance Season 4 Details, Episode Descriptions, and Air Dates

Season four of HBO’s High Maintenance, the half-hour comedy created by Katja Blichfeld and series star Ben Sinclair, will premiere on February 7, 2020. The new season consists of nine episodes and will air on Fridays at 11pm ET/PT.

HBO’s revealed details on the first two episodes of season four which will feature returning guest stars Crystal Monee Hall, Heléne Yorke, Ken Leung, Julianna Luna Vasquez, Avery Monsen, Rob Morgan, Max Jenkins, Chris Roberti, Becca Blackwell, Chris McKinney and Birgit Huppuch. Ira Glass and his team at This American Life, Nick Kroll, Rebecca Hall, Larry Owens, and Calvin Leon Smith will join the series as guest stars in the new season.

  • Season 4, episode 1: “Cycles”
    Debut date: FRIDAY, FEB. 7 (11:00-11:30 p.m. ET/PT)
    The Guy (Ben Sinclair) finds a lost canine. A new reporter at This American Life, Yara (Natalie Woolams-Torres) pitches a story about her parents’ marriage and inadvertently strains her own relationship when her boyfriend Owen (Marcus Raye Pérez ) visits for their anniversary weekend. A singing telegram (Larry Owens) in a bad mood looks for some relief while crisscrossing the city on a crazed workday.
    Written by Ben Sinclair; directed by Ben Sinclair.
  • Season 4, episode 2: “Trick”
    Debut date: FRIDAY, FEB. 14 (11:00-11:30 p.m. ET/PT)
    The Guy (Ben Sinclair), with new friend “Fomo” in tow, delivers to Matthew (Calvin Leon Smith), a man looking for a connection who hires a new-to-the-business escort (Jay Jurden) for the night. After bonding on set with a familiar face, intimacy coordinator Kym (Abigail Bengson) learns a surprising fact about her new love interest that threatens to derail their romance just as it’s beginning.
    Written by Isaac Oliver; directed by Katja Blichfeld.

High Maintenance Plot:

High Maintenance continues to paint a unique and loving portrait of New York City, exploring the often-messy interpersonal moments of everyday people who are looking for meaning, companionship and a little high to make it through the day.

This season finds The Guy (Sinclair) back traversing the city on his bicycle, having said goodbye to last season’s RV. With a new friend by his side, The Guy drops in on a variety of customers whose disparate lives, jobs, identities and circumstances reveal the human connection that we all seek.

Playing out over the course of a year, this season focuses on cycles of renewal, webs of human connections, and putting down roots in the ever-changing ecosystem of New York City.