1. Jo was Dean’s biggest regret; we see this in “Defending Your Life,” we know that Osiris only asks about things that Dean regrets. Osiris asks several times about Jo’s feelings for Dean, in comparison he only asks once about Jo’s first case; atau the one that started it all. menunjukkan Dean regrets something about her feelings for him. Which would either mean he feels he lead her on, atau he he would feel guilty for never reciprocating. telah diberi the look he gave her when he joked about her “massive crush” on him, he felt guilty for never reciprocating.