On the day of an 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.

A computer programmer tries out a tech-free night per the Guy's advice; a comic's controversial tweet draws the attention of Internet trolls; a fearless dancer attempting to match a world record struggles as her dance partners fall by the wayside.

A man turns to the Guy to get a prescription for his high-strung wife, not to mention something for their underwhelming sex life; the Guy gets more than he bargained for when tries to help out an elderly man.

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.

Abdullah, a potential partner, takes over the Guy's weed route while he attempts to take time off.

The Guy tries to de-stress when he ends up in an uncomfortable situation. A freelance brand strategist (Kate Lyn Sheil) struggling with her latest assignment embarks on a desperate search for a weed fix.

An ex-Hasidic man (Luzer Twersky) explores the world outside his sect as he connects with a writer who may have ulterior motives. A nightclub performer's (Darrell Thorne) night out takes an unexpected turn. The Guy bonds with a driver (Abdullah Saeed) when he finds himself in need of a lift.

An industrious Brooklyn realtor (Danielle Brooks) 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.

A couple (Marcia DeBonis, Ray Anthony Thomas) visiting their daughter (Amanda Debraux) 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.

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 (Joshua Schubart) struggles to maintain his commitment to losing weight.