After Dean's vampire companion in Purgatory, Benny (guest star TY OLSSON) gets brutally beat up by his own kind, he calls Dean for help. Dean abruptly packs up and tells a confused Sam that he's taking a "personal day." Benny confesses that he's going after his Maker (guest star PATRICK STAFFORD) so Dean offers to help, flashing back on the many times Benny helped him and Castiel in Purgatory. Meanwhile, Sam uses his solo time to reflect on the life he left behind with Amelia (guest star LIANE BALABAN). However, when things go bad for Dean and Benny, Dean summons Sam for help... making everything very complicated.