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.

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.

Young Raymond tries his best to be useful on a day off from school. Barbie, a long-time 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 started an affair.

When a stylish septuagenarian gets an unexpected offer to model in an ad campaign, she finds that the experience makes her more self-conscious about her age. A veterinarian suffering from depression decides to try micro-dosing mushrooms, with some advice from The Guy.

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.

Married couple Adriana and Arturo get a special delivery that changes their family dynamic. An aspiring dancer questions her future as a nanny to two motherless kids.

An acting teacher named Leonard contemplates a move 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 has a busy day as New Yorkers react to world-changing news. Carefree hotel guests spend an indulgent day, unaware of what's going on outside their door. With the world 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 endeavours 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 takes over control of The Guy's marijuana distribution route while he takes time off.

Emily, an artistic teen, has her birthday spotlight stolen by her bohemian mother, her sexual, uninhibited friends, and a delivery from The Guy. Only her mother's European friend gives her the attention she craves.

A husband turns to The Guy to get a prescription for his highly-strung wife and her stress levels, 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.

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. Attempting a world record, a dancer struggles as the hours drag on and her partners fall by the wayside.

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.