No. Not at all. He has loved Ruby for a long time, enjoyed a long life with her full of happy memories, shared every piece of himself with her on a level very few could understand. In simple terms, he's no different than a lover or a spirit that can't let go. That's--That's why sex with Madison didn't go over so well when he spouted Ruby's name in the middle (a detail he isn't sharing). He's quiet for a long time.

"No. I'm ready to move on from Ruby, Dean." Which is about all he can say as the rest of what advice he's been given sits rather poorly with him, as evidenced in how tight his lips grow together. "I don't care what's supposed to happen. What I want is some connection with her again. I miss her every day." He knows Dean means well though. Had it been anyone else's story, he would agree that moving on is the option.