When her father was killed, she contacted Dean for help and they eventually renewed their relationship by sleeping together, although Dean soon left town again.
In Dean's fantasy world, Carmen was his live-in girlfriend. She knew almost everything about him (his favorite beer and foods).
After defeating Abaddon with Henry's help, Dean is shown to enjoy the idea that Abaddon will be forever trapped due to their inability to kill her.
After Abaddon escapes, she tries to get Dean to give her the location of Crowley and tells him that she finds Dean a worthy vessel.
“This was just straight up in your face, not computerized, old school stunts. I would burn down the world.” “My hair,” Winters said.
Dean meets Anna during the fourth season, and protects her from angels and demons and soon discovers that she is an angel herself.They are on friendly terms until Anna goes back in time to kill Mary and John. Dean later witnesses her death at the hands of Michael.Dean first met Cassie in Athens, Ohio, where she was at college and he was on a hunting mission.During their final battle, Dean snarls as he kills Abaddon with the First Blade and then viciously attacks and mutilates her body after she's dead before being snapped out of it by Sam.Dean met Alastair after he was dragged off to Hell by a hellhound.