In the tunnels beneath Hawthorne House, Avery Grambs and Jameson Hawthorne privately revisit Avery's first meeting with Harry, the homeless man she played chess with after her mother's funeral. Avery recalls finding him near a park pond, intervening before a police officer reached him, and asking him to play chess; they continued playing regularly, though Harry never revealed more than a false name.

Jameson presses Avery because they now believe Harry was actually Toby Hawthorne, Tobias Hawthorne's supposedly dead son. Avery reflects on how recently her life changed: Tobias left her nearly his entire fortune, and she and Jameson followed his clues to an apparent answer involving her name, her birthday, and Tobias's hope that she could repair his family.

Jameson suggests the inheritance mystery may not be solved. He theorizes that Tobias once visited the Connecticut diner where Avery's mother worked not by chance, but while searching for Toby, and that Tobias may have discovered Avery through that search. Avery questions whether the clues about her name and Emily's death were lies or misdirection.

Avery resists Jameson's charm and proposes a competing possibility: perhaps Tobias did not know Toby was alive, and Toby was the one who noticed Tobias watching Avery and considering her as heir. Jameson senses Avery may be withholding something, then argues that they need rules and stakes to solve the mystery. He proposes a wager: if he solves it first, Avery must forgive him for abandoning her emotionally after the Black Wood revelation; if Avery wins, Jameson must forget their kiss and stop trying to charm her into another one. Jameson accepts, declaring the game on.