‘High Maintenance’ Season 2: Episode Guide, Plot Details, and Cast Info

High Maintenance Season 2 Episodes
Ben Sinclair in ‘High Maintenance’ season 2 episode 1 (Photo by David Giesbrecht / HBO)

Season two of the HBO comedy series High Maintenance will premiere on Friday, January 19, 2018 at 11pm ET/PT. The half-hour comedy was created by Katja Blichfeld (30 Rock) and Ben Sinclair (Home Again, Sisters), and stars Ben Sinclair as a pot-dealing deliveryman. In support of the upcoming new season, the network’s released details on January and February episodes as well the second season’s guest stars.

Danielle Brooks (Orange Is the New Black), John Gallagher, Jr. (The Newsroom), Jessica Hecht (The Forgotten), Luzer Twersky (Félix & Meira) and Kate Lyn Sheil (Girlfriend) will make their High Maintenance debuts in season two. Season one’s Abdullah Saeed (Bong Appétit) and Yael Stone (Orange Is the New Black) return as guest stars.

Season one of the half-hour comedy consisted of six episodes, and season two has an expanded order of 10 episodes. Blichfeld and Sinclair executive produce the critically acclaimed comedy along with Russell Gregory. Willy Friedman, Gwen Bialic and Emi Irikawa serve as producers.

The Season 2 Plot: A comedy of human interaction, the new season of High Maintenance delves deeper into the contemporary anxieties New Yorkers are experiencing, from political tension to soaring real estate prices, while emphasizing the importance of savoring the highs of life in this increasingly volatile world. Pulling back the curtain on The Guy’s personal life, the second season reveals a few more people and details of what happens when he’s not on the clock.

Introducing new customers and revisiting familiar ones, the second season of High Maintenance weaves together a labyrinth of humor, poignant observations and heartfelt moments in stories that explore the lives of intriguing and colorful individuals from all walks of life.


High Maintenance Season 2 Episodes:

Episode #7: “Globo” (season 2, episode 1)
Debut: FRIDAY, JAN. 19 (11:00-11:30 p.m. ET/PT)
The Guy (Ben Sinclair) has a busier-than-usual day as New Yorkers react to world-changing news. The morning after a hookup, carefree hotel guests spend an indulgent day, unaware of what’s going on outside their door. With the world around him in disarray, a client’s roommate (Joshua Schubart) struggles to maintain his commitment to losing weight.
Written and directed by Katja Blichfeld and Ben Sinclair.

Episode #8: “Fagin” (season 2, episode 2)
Debut: FRIDAY, JAN. 26 (11:00-11:30 p.m.)
A couple (Marcia DeBonis, Ray Anthony Thomas) visiting their daughter (Amanda Debraux) in Bushwick embraces the urban surroundings while dealing with a less-than-ideal rental that comes with an unwelcome roommate. The Guy (Ben Sinclair) delivers to Brenna (Brenna Palughi) and Molly’s (Molly Knefel) all-female, politically-minded meetup, where things get dramatic fast.
Written by Rebecca Drysdale & Isaac Oliver and Katja Blichfeld & Ben Sinclair; directed by Katja Blichfeld & Ben Sinclair.

Episode #9: “Namaste” (season 2, episode 3)
Debut: FRIDAY, FEB. 2 (11:00-11:30 p.m.)
An industrious Brooklyn realtor (Danielle Brooks) endeavors to hustle her way to a new home. After winning an affordable-housing lottery, Candace (Candace Thompson) and John (John E. Peery) face culture shock and notice a class divide when they move into their new apartment. The Guy (Ben Sinclair) considers his living situation.
Written by Hannah Bos, Paul Thureen and Shaka King; directed by Shaka King.

Episode #10: “Derech” (season 2, episode 4)
Debut: FRIDAY, FEB. 9 (11:00-11:30 p.m.)
An ex-Hasidic man (Luzer Twersky) explores the world outside his sect as he connects with a writer who may have ulterior motives. A nightclub performer’s (Darrell Thorne) night out takes an unexpected turn. The Guy (Ben Sinclair) bonds with a driver (Abdullah Saeed) when he finds himself in need of a lift.
Written by Ben Sinclair; directed by Shaka King.

Episode #11: “Scromple” (season 2, episode 5)
Debut: FRIDAY, FEB. 16 (11:00-11:30 p.m.)
The Guy (Ben Sinclair) tries to de-stress when he ends up in an uncomfortable situation. A freelance brand strategist (Kate Lyn Sheil) struggling with her latest assignment embarks on a desperate search for a weed fix.
Written by Katja Blichfeld and Rebecca Drysdale; directed by Katja Blichfeld and Ben Sinclair.