Simon joins the Bridgertons on their Greenwich boating outing. Daphne apologizes for Violet’s machinations, but Simon assures her that he did not accept Violet’s invitation out of obligation. Skeptical, Daphne declares, “‘And this from a man who is feigning a courtship to me, of all people, all because he’s too polite to refuse invitations from his friends’ new wives” (152). Simon asks what she means by “me, of all people,” and Daphne is charmed by his refusal to accept her self-deprecation. As they exit the boat, Simon becomes captivated by Daphne’s beauty, nearly leaning forward to kiss her before Anthony sweeps Daphne away.

On the outing, Simon does not know what to make of the Bridgerton family dynamics. Daphne says she cannot imagine life with no siblings or parents, then worries she has slighted Simon. Simon insists he does not regret his lack of a family, but Daphne is unconvinced, noticing a distant look in his eyes. She wishes to comfort him with an embrace.

During the family’s picnic, Hyacinth tells Simon a story about Sir Walter Raleigh ruining his cloak so that the Queen would not ruin her slippers. Simon playfully looks for puddles, asking if he should remove his shirt to save Hyacinth any distress.