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.

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

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.

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.

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

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.

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.

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.

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.

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.

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.

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.

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

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

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.

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.

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