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.