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.