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While visiting Sonny's place, Dean found Robin with Timmy, a boy who was being haunted by a ghost.
Dean asked Robin to trust her of the danger but she was reluctant to have anything to do with Dean and revealed she remembered him but Dean forced her to cooperate as he tried - with Timmy's help - to convince the spirit of Timmy's mother to move on.
Robin was shocked by the sight of an actual ghost and that Dean fights monsters everyday.
She was nearly attacked but watched as Dean protected her and convince Timmy to have the ghost move on and was successful.
After Dean and Sam rescued John, Azazel revealed himself to be in possession of their father and pinned the two of them to opposite walls.
Azazel expressed a desire to murder Dean with John's own hands in retaliation for what Dean did to Meg and Tom, revealing the pair to be his own children.
Dean promised to take her to the homecoming dance, though Dean's father forced him to leave the area.In the real world, she was a model in a magazine for his favorite beer.Dying from an inoperable brain tumor, Layla and her mother were frequent visitors to Roy Le Grange's church in the hope that he would heal her.Whenever Anna pops in, Dean is surprised to see her, but treats her kindly, even going so far as to compliment her appearance on one such occasion.They were on friendly terms until Anna goes back in time to kill Mary and John so that Sam could never born.