|Dates||???? - 2015 (killed by Len Fletcher)|
|Location||Fall River, Massachusetts|
|Episode(s)||11.05 Thin Lizzie|
Sydney was a young woman living in Fall River, Massachusetts. After her boyfriend dumps her, she comes across a young Amara in a bar parking lot, seeing that Sydney is sad Amara attempts to make her happy by giving her instant bliss. Thankful for what she did, Sydney asks Amara if she is an angel, which angers her, prompting Amara to take her soul.
When Sam and Dean come is investigating the death of Mr. Pinksy, Sydney tells him that Mrs. Pinksy has a lover and gives Sam his address. When Sam and Dean get there Mrs. Pinksy and her boyfriend are dead. Sam finds the Pinsky's son, Jordan, tied up in a closet. While helping him out of his bindings, he places his weapon down. When the boy looks behind Sam, Sam turns around to find Sydney is there cocking a shotgun and aiming it at him. Prompting Sam to raise his hands in surrender.
Dean comes to and realizes that he and Sam are now tied up. Sam informs Dean that it is Sydney the babysitter who’s lost her soul. Sydney tells the boys that they are an offering for Amara. She tells them she killed the couple because that was the guy who'd dumped her, she killed the woman who ran the B&B because Sydney used to work there and she screwed her out of two weeks’ pay. Then she starts on the boy’s parents, saying she was going to take care better care of Jordy than either of them. Telling them how she feels like a new person after meeting Amara, and goes on to tell them her parents were abusive, and with Amara she didn’t remember the pain or memories or care about the scars on her body. When Dean sees Sam is almost out of his bindings, he starts provoking Sydney with questions about Amara. When Sydney strikes Dean with the shotgun Sam jumps from his chair and grabs a wrench from the workbench. Sydney fires the shotgun at Sam, who ducks just in time. Sydney collapses -- Len is standing behind her with a bloody hatchet. Disbelieving he just actually killed someone, Len hands the hatchey over to Sam. While Sydney is lying on the floor bleeding out she tells them, "The Darkness is coming, it’s so peaceful. It’s coming for all of us."