Leonard, an acting teacher, contemplates moving back to New York. The Guy connects with old high-school friends Sarah and Brian, who are visiting the city under difficult circumstances.

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

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.

A fashionable older woman agrees to model in an ad campaign while a veterinarian suffering from depression experiments with microdosing mushrooms.

The introduction of money to a couple's sex life leads them down a delightful yet risky path; with her husband out of town, Karen Farad uses her fellow teachers and a visit from the Guy to escape her daily routine.

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.

An eager young man tries to help his mom at work while Arthur, a nudist, gets a new roommate.

After his bike is stolen, regular customer Marty consults The Guy, whose suggestion sends him down a surprising path. Bored with her mundane life, Darby finds ways to unnerve and bewilder strangers.

While spending time away from the city in his RV, The Guy gets upsetting news, but makes an intriguing new connection. Cori, meanwhile, tries to adjust to a new reality without her friend.