Following James Ponder’s instructions, Mrs. Gidley researches addresses for three portrait recipients, mails Theo’s handwritten invitations, and starts a delivery log to track timing. The work feels demeaning to her and deepens her suspicion about why Theo is giving away valuable portraits, even as she notices his unusually beautiful handwriting.

At the Fedder fountain, Theo conducts bestowal number two with Junior Perryman, a one-armed mixologist at the Bowleg Bar and Grill. Junior chats easily, jokes about bartending with one arm, and tells Theo the fountain’s “Peeth a Fedder” origin story. When Theo finally presents the portrait, Junior accepts with surprised gratitude and invites Theo to visit the bar, planning to give the portrait to his mother.

Bestowal number three goes to Bun Everson, a University of Golden graphic design student who arrives with her friend Sara, an English major and aspiring writer who previously wrote an article about Asher. The two share dreams of starting a magazine and recognize the portrait from the Chalice wall, explaining they had spoken with artist Mr. Glissen when he photographed them. Theo realizes this meeting may lead to future encounters—and the narrative notes it later becomes part of their magazine’s story.

Before bestowal number four, the chapter recounts James Ponder’s cautions: Theo should not write directly to children and should be careful giving portraits to women, especially young women, because such gestures can be misunderstood. Despite the risk, Theo proceeds because Frankie Knowles’s portrait feels important.

Frankie, a twelve-year-old in a wheelchair, arrives with his parents, who are wary because they rarely visit the Chalice and did not know Frankie’s photo had been displayed. Theo speaks with Frankie warmly and attentively, learning Frankie loves NASCAR. When the family sees the portrait, Frankie’s mother is overwhelmed and Frankie’s father quietly beams; the moment ends with thanks, hugs, and laughter. Theo never sees them again, but the family spreads the story, confirming that Theo’s giveaway mission has momentum, with many portraits still to return.