When Chase and his sensitive yet fun-loving dog Gatsby move from the suburban Midwest to Queens, culture shock takes its toll – until they cross paths with Beth, a whimsical dog walker.

The Guy finds a lost canine. A reporter pitches a story about her parents' marriage and inadvertently strains her own relationship when her boyfriend visits for their anniversary weekend. A singing telegram in a bad mood looks for some relief.

The Guy delivers to Matthew, a man looking for a connection who hires a new-to-the-business escort for the night. After bonding on set with a familiar face, intimacy coordinator Kym learns a surprising fact about her new love interest.

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.

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.

An acting teacher returns to New York with his class and The Guy reconnects with a pair of high-school friends.

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.

Snowed-in flight attendants spend Christmas Eve together; The Guy is delayed on his way home for the holidays.

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.

Two sisters clean out their childhood home after the untimely death of their mother. The Guy delivers to a bickering couple renegotiating their relationship. And a new mother hosts her teenage cousin from out of town.

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.

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.

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.

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.

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

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.

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.

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.

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