When The Guy and his eclectic jury duty group head to a karaoke bar to mark the end of their civic service, Keesha and Roman, the youngest members of the crew, run into trouble. While exploring a side hustle with her friend Violet, Freddie encounters someone from her past.

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.

The Guy visits a film set and Lee struggles through a bad day in New York.

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.

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.

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.

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.

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.

A couple adjusts to life with a special delivery and The Guy hangs with a young nanny.

The Guy encounters two teachers who just started an affair and a couple trades sexual experiences for money.

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.

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.

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.

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.

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.

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.

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.

A fashionable older woman models in an ad campaign and The Guy advises a veterinarian who wants to try micro-dosing.

After his bike is stolen, regular customer Marty consults The Guy, whose suggestion sends Marty down a surprising path. Bored with her mundane life, Darby finds various ways to unnerve and bewilder strangers.

A construction worker develops a crush, a roller-blader tries to save a fireworks display and The Guy and Lee attend a themed boat party.

The Guy pays a visit to agoraphobic Patrick, a longtime customer. The Guy seeks solace from a customer after a rough night.

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.

While spending some time in his RV and away from the city, The Guy gets some upsetting news but makes an intriguing new connection. Cori, meanwhile, is trying to adjust to a new reality without her friend.

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.

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.