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A brand strategist and The Guy’s ex-wife, Jules pays him a visit after receiving unwelcome news. She’s also on a mission to get high, despite her girlfriend Gwen’s disapproval.

A free spirit who constantly moves from one living situation to another. Chad is both a client and The Guy’s friend. He currently resides in a black box theater.

A whimsical dog walker who inspires a special connection with one of the dogs she cares for named Gatsby.

Flustered by his inability to find the key to his apartment, Art asks The Guy to lend him a hand.

A Westernized, first-generation college student, who lives with her moderately religious aunt and uncle. Eesha tows the line between responding to her secular desires and upholding her family’s values, but her duality begins to falter when her weed connection bails.

Acting teacher Leonard returns to New York City with his class and contemplates making the move permanent.

Next-door neighbor of The Guy with her live-in girlfriend Jules, Gwen disapproves when Jules smokes pot.

Ronald is excited to visit his daughter Claire and see her neighborhood. He’s just not too sure about the surprise roommate occupying the Airbnb where he and his wife, Sharon, are staying.

A retired former workaholic who lives downstairs from his neurotic daughter, Quinn, and her husband and baby.

While he’s not as experienced playing dress-up as his wife, Dahlia, Apollo is game to don a disguise to help his sister-in-law with a surprise.

Conflicted about his addiction to the internet and technology, Jasper trades in Twitter for paperbacks and his smartphone for a flip phone. Habits, however, are hard to break.

A free-spirit, Monica is oblivious to the troublesome news happening outside her hotel room door, thanks to preoccupations left over from the night before.

A client of The Guy’s, Renee is excited to treat her daughter Emily and her friends to some of The Guy’s finest products, before leaving for a night on the town. 

An agoraphobic, Patrick is one of The Guy’s longtime customers and is coping with the death of his mother.

In a co-dependent relationship with his best friend since college, Lainey, Max is dubbed “Asshole” on The Guy’s client list. He begins to turn over a new leaf after meeting a great guy on a sex app.

Sharon is overjoyed to visit her daughter Claire and stay in a hip Airbnb with her husband, Ronald. Unfazed by their surprise roommate, she’s looking forward to a city adventure.

Baruch has recently left his Hasidic Jewish community in search for something more. An eccentric writer looking for her next story is intrigued by his background.

Part of a jaded couple who are throwing an intimate birthday celebration. Leo's plans are thrown for a loop when he visits the doctor and gets a troubling diagnosis.

A writer who hits it big with a television series based on one of his past relationships.

The aging mother of a musical prodigy, Joon navigates her son’s recent success and new lifestyle.

Depressed and detached, veterinarian Gene experiments with micro-dosing mushrooms, but quickly gets in over his head.

A macho actor whose preparation for a role puts stain on his romantic relationship and scares off The Guy during a delivery.

Emily’s most outgoing and confident friend, Zoey, brings a half-drank bottle of tequila, asks Renee for edibles, and gives stick and poke tattoos to her friends.

Mamie, a local business owner and stylish septuagenarian, agrees to model for a body-positive ad campaign — only to be reminded of her age.

After a tweet backfires, a comedian gets harrassed by Twitter trolls.

Cody, Brian’s roommate, is determined to get through spin class and continue the healthy-eating habits that have propelled his weight loss.

Ira looks to The Guy for a product that will help his wife, Laurie, relax and focus on their relationship and not their college-age daughter. 

John has doubts about the sudden, and drastically different, lifestyle change he and his girlfriend, Candace, experience.

A longtime friend of The Guy, Bryan and his wife Sarah visit New York City under difficult circumstances.

Eager to spend a day in the park with his girlfriend, Alina, but angered by his mother’s conservative views on Facebook, Zach hopes the eclipse will take his mind off things.

A helicopter mother, Laurie is desperate to know her daughter’s every move while she’s away at school. Her husband, Ira, is desperate to get her to relax. 

A tireless kitchen worker by day and barback by night, Luiz is focused on only one thing: making it through his shifts to see his son Luca.

A twenty-something aspiring journalist who spends most of her time on social media. She convinces The Guy to sit down for a one-on-one interview, but is unable to contain her social media addiction, which threatens to blow up the story.

In a co-dependent relationship with her best friend since college, Max, Lainey is controlling and demanding. She becomes highly suspicious when Max begins to spend more and more time doing things without her.

Husband to strong-willed Adriana, Arturo learns to adapt to their new family dynamic after receiving a special delivery.

One of The Guy’s former customers, Heidi finds herself confronted by a past relationship and decides to seek legal help (and to enlist The Guy) to resolve the matter.

A soft-spoken teenage artist, Emily celebrates her birthday with her uninhibited friends, her flighty mother, Renee and her mother’s intriguing friend, Claudia. 

A regular client of The Guy, Marty goes down a Craigslist wormhole after his bike gets stolen.

Eager to be helpful on his day off from school, precocious Raymond lends his mother a hand at her job.

A resident of upstate New York, Cori mourns the loss of her neighbor, Berg, who was like family to her. 

A performer at a Brooklyn nightlife venue, Lawrence finds himself in an unlikely situation after one of his shows.

A steadfast Brooklyn real estate broker, Regine knows how to close a deal in an ever-changing borough with increasingly diverse clients. When her weed dealer fails to deliver a variety of products, she sees if The Guy has something better to offer.

The aging father of a musical prodigy, Wei navigates his son’s recent success and new lifestyle.

Attentive nanny to motherless siblings Eli and Ana, Erin struggles to balance her demanding day job with getting her dance career off the ground.

New to New York from Puerto Rico, Oscar takes up a Rockaways-based construction job, where he develops a crush on a local bodega worker.

Claudia, a filmmaker, crashes with Renee while on assignment in New York. She’s impressed by Renee’s daughter, Emily.

Bored with her mundane life as an office assistant, Darby seeks to unnerve and bewilder strangers.

A friend of The Guy's from high school, Sarah visits New York City with husband Bryan under difficult circumstances.

While living in communal housing with boyfriend John, Candace is offered a life-changing opportunity that places them both outside their comfort zones.

A neurotic mom who brings her family to live upstairs from her dad in a Brooklyn townhouse. Under the same roof as her dad again, she clashes with his newfound free-spirit lifestyle.

Brian, a client of The Guy, has difficulty coping with some disturbing news. His roommate, Cody, however, is preoccupied with his weight-loss regimen.

A sensitive yet fun-loving dog that struggles with the culture shock of moving from the suburban Midwest to Queens.

A compassionate pot dealer who serves as both supplier and emotional confidante to his diverse array of clients.

Previously seen in Episodes “Ex” and “Googie,” Arthur is a nudist without a roommate — and decides to give cohabitation with eccentric Barbie a try.

Helping her sister, Alina, with a surprise in the park, Dahlia gets a thrill getting dressed up to go incognito and using a fancy new camera.

After Leo’s infamous birthday party in Season 1’s “Museebat”, in Season 3’s “Breathwork,” producer Gigi must keep a doomed film set from the verge of collapse.

Daughter of Ronald and Sharon, Claire hooks her parents up with a chic Airbnb loft for the weekend. Her friends call The Guy — and she gets to see her parents in a different, looser light.

Alina, already nervous about her surprise eclipse day plans, grows anxious when a group of pot-smokers take over the spot she had hoped to claim with her boyfriend, Zach.

When her attempt to break a world record becomes more difficult then she thought, Gloria’s lover Jim enlists the Guy to bring her some motivation.

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The Guy

Played by Ben Sinclair

A compassionate pot dealer who serves as both supplier and emotional confidante to his diverse array of clients.

About the Series

High Maintenance

Featured Characters

See All

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