The Guy makes an uncomfortable delivery to a macho client and his taciturn friend. Best friends Max and Lainey’s co-dependent relationship begins to wane after Max accidentally stumbles upon a new group of friends. In order to stay part of this group, Max must maintain a charade, while keeping Lainey’s suspicions at bay.
Eesha, a young girl living with her aunt and uncle in Brooklyn, struggles to be a “normal college student,” despite her family’s religious values. The Guy delivers to Leo and Gigi, a jaded couple throwing an intimate gathering for Leo’s birthday – an event marked by accusations, recriminations and a troubling revelation.
When Chase and his sensitive yet fun-loving dog Gatsby move from the suburban Midwest to Queens, culture shock takes its toll – until they cross paths with Beth, a whimsical dog walker.
Aging parents Joon and Wei navigate their son’s recent success and new lifestyle. The Guy delivers to Jim, a retired, former workaholic living downstairs from his neurotic daughter, Quinn, and her husband and baby.
Anja, a twentysomething aspiring writer who spends most of her time on social media, convinces The Guy to sit down for a one-on-one interview, but her social media addiction threatens to blow up the story. Former customer Heidi enlists The Guy’s help when she is confronted by her past.
The Guy pays a visit to agoraphobic Patrick, a longtime customer. The Guy seeks solace from a customer after a rough night.
The Guy 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 struggles to maintain his commitment to losing weight.
A couple visiting their daughter in Bushwick embraces the urban surroundings while dealing with a less-than-ideal rental that comes with an unwelcome roommate. The Guy delivers to Brenna and Molly’s all-female, politically-minded meetup, where things get dramatic fast.
An industrious Brooklyn realtor endeavors to hustle her way to a new home. After winning an affordable-housing lottery, Candace and John face culture shock and notice a class divide when they move into their new apartment. The Guy considers his living situation.
An ex-Hasidic man explores the world outside his sect as he connects with a writer who may have ulterior motives. A nightclub performer’s night out takes an unexpected turn. The Guy bonds with a driver when he finds himself in need of a lift.
The Guy tries to de-stress when he ends up in an uncomfortable situation. A freelance brand strategist struggling with her latest assignment embarks on a desperate search for a weed fix.
Abdullah, a potential partner, takes over the Guy's weed route while he attempts to take time off.
Emily, an artistic teen, has her birthday spotlight stolen by her bohemian mother, her uninhibited friends and a delivery from the Guy; only her mother's European friend gives Emily the attention she craves.
When a high-strung mother finds herself more involved in her college-aged daughter's life than her own, her husband turns to The Guy to get a prescription for her stress, not to mention their underwhelming sex life. After a routine delivery, The Guy's good deed helping out an elderly man turns into more than he bargained for.
Deciding to embrace a life without the distractions of the Internet, a computer programmer tries out a tech-free night per The Guy's advice. After a controversial tweet draws attention, a comedian becomes inundated by Internet trolls. While attempting to match a world record, a fearless dancer struggles as the hours drag on and her dance partners fall by the wayside.
Season finale. On the day of the eclipse, two couples head to the park and make new friends in the process. The Guy says some goodbyes and attempts to make a few life changes.
While spending time away from the city in his RV, The Guy gets upsetting news, but makes an intriguing new connection. Cori, meanwhile, tries to adjust to a new reality without her friend.
After his bike is stolen, regular customer Marty consults The Guy, whose suggestion sends him down a surprising path. Bored with her mundane life, Darby finds ways to unnerve and bewilder strangers.
Young Raymond tries his best to be useful on a day off from school. Barbie, a longtime New Yorker, must find a new place to live and becomes roommates with The Guy's nudist client, Arthur.
The Guy delivers to a film set, where cast and crew are struggling to make it through a day of reshoots. Lee returns to New York City, but has a hard time putting the past behind her.
Ayasha and Doc, a BDSM-inclined couple, decide to start trading sexual experiences for money in their relationship. After discovering he’s internationally known, The Guy pays a visit to a pair of summer-school teachers who have just begun an affair.
When Mamie, a stylish septuagenarian, gets an unexpected offer to model in an ad campaign, she finds the experience makes her more self-conscious about her age. Meanwhile, a veterinarian suffering from depression decides to try microdosing mushrooms, with some advice from The Guy — but quickly builds up a tolerance.
Oscar, a recent arrival from Puerto Rico, starts a construction job and develops a crush on a bodega worker. Sophia steps up when her family’s annual fireworks display hits a snag. The Guy and Lee attend a “Holidazzle” boat party, where they run into a familiar face.
Husband-and-wife Adriana and Arturo get a special delivery that changes their family dynamic while an aspiring dancer questions her future as a nanny to two motherless kids.
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.
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.
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 and his eclectic jury duty group head to a karaoke bar to mark the end of their civic service, but Keesha and Roman, the youngest members of the crew, run into trouble. While exploring a side hustle with friend Violet, Freddie encounters someone from her past.
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.
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 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.
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.
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.
Snowed-in flight attendants spend Christmas Eve together; The Guy is delayed on his way home for the holidays.
The Guy starts things off on the wrong foot when he visits the hotel room of Stevie, a woman with clinical anxiety and a very impatient boss.
Heidi and Mark are an adorable new couple, and everything seems perfect until they call The Guy for marijuana delivery.
The Guy meets Jamie when he delivers to a pair of women who are upset due to having a mouse in their apartment.
The Guy reluctantly delivers to a man and woman listed in his phonebook as "Assholes" and who have an artist friend named Olivia.
The Guy delivers to an agoraphobic man who lives with his mother and is obsessed with Helen.
The Guy hears a story about Trixie when he delivers to a couple who are stressed out because of their inconsiderate AirBnB guests.
A couple's relationship is stressed by the overstay of their house guest, an old friend who's in town for Dinah's wedding. Meanwhile, The Guy catches them at an awkward time after delivering to an asexual magician.
Hannibal Buress stars as himself, a stand-up comic trying to get over a traumatic experience, and The Guy tries to cheer him up. Meanwhile, Heidi returns for a cameo role, discussing Jonathan with Hannibal's artist girlfriend, Olivia.
A private chef is hired to serve a Passover Seder dinner, and one of the family members happens to be the asexual magician. The chef calls The Guy for delivery, and he arrives just in time to learn about Elijah.
An uptight woman discusses Brad Pitts with her bird-watching friend who she discovers is very ill. She suggests that they smoke marijuana together to help with her friend's low appetite. Meanwhile, The Guy gets high with a pair of professional stoners.
One of The Guy's customers start dating a fitness buff. She soon learns about his very alternative lifestyle and about Qasim. Meanwhile, The Guy dresses as himself for Halloween.
For the first time, The Guy is the central character. He struggles to entertain his teen-aged niece who is visiting from out of town. He doesn't want to conduct business in front of her, but when their plans to see "Matilda" get complicated, one of his customers offers to help out. Featuring cameos from a few characters from the "Jamie" episode.
A cross-dressing author struggles with writers' block, which puts a strain on his marriage. Meanwhile, The Guy makes a delivery to him and is introduced to Rachel. Featuring cameos from characters from the "Trixie" and "Olivia" episodes.
The guy plays matchmaker, sending two middle-aged marijuana enthusiasts go on a first date.
A woman struggles with her fiancé’s increasing paranoia and survivalist tendencies.
A frustrated cubicle-working idealist tries to make a difference in the world by becoming a teacher. His attempts fall flat and the experience challenges his optimism.
Reagan and Ezra get priced out of Williamsburg and head to a more affordable neighborhood where they learn you can't have it all when it comes to NY real estate.
A hapless weed delivery girl named Orly fumbles her way through various misguided pursuits, stealing some of The Guy's customers along the way.
Six long-time friends escape the city and head upstate for a weekend where they spend more time worrying about their careers than enjoying themselves.
