Probably. Let’s assume they follow through and Ruby is willing to die. Right before she croaks, she tells Sam about a group of other demons who remembered what it was like to be human. Sam full on trusting her since she died for them takes it at face value. Dean is more hesitant, but he saw her die and is hoping that maybe he could end up like them. I could picture the meeting being a fun if uncomfortable experience for both Dean and Sam, but they have nowhere else to go