|Dates||???? - 2013 (taken off life support)|
|Episode(s)||8.20 Pac-Man Fever|
Gertrude Middleton was married with a daughter Charlie (not her real name), to whom she would often read The Hobbit at bedtime. This led to Charlie becoming interested in fantasy and science fiction.
When she was twelve, Charlie got scared at a sleepover and called her parents to come pick her up. On the way, they were hit by a drunk driver and her father was killed while her mother was left brain-dead and kept alive on life-support. Afterwards, Charlie hacked into a game company's server and stole an unfinished first-person shooter game called The Red Scare that pits the player against super-soldier vampires. She reprogrammed it to reflect her "flamingly liberal politics" and released it for free. She was eventually tracked down and arrested, forcing her to go on the run for 16 years. During that time, Charlie secretly visited her mother and read to her while using her aliases to fund her mother's hospital bills.
When Charlie disappears during the case they are on, Sam and Dean find her apartment and discover her multiple identities and the donations to Gertrude Middleton. Dean visits the hospital, and a nurse tells Dean how she ended up in the hospital, and that other nurses have reported that sometimes someone visits her and reads to her.
When the djinn traps Charlie in a nightmare, Dean follows her in. Charlie leads Dean to the patients, where Dean finds one is Charlie's mother and another is Sam. Dean explains how after Charlie disappeared he learned about her mother and realizes that her greatest fear isn't the video game or what it did to her, it's losing her mother. Charlie tells Dean she believes what happened to her parents is her fault and that she wants to apologize to her mother and tell her she loves her and have her understand, but knows that will never happen. Dean is sympathetic and convinces Charlie to let go of her mother as she is long gone. Once Charlie does so, the loop is broken and they return to the real world where Sam has killed the other djinn. Charlie breaks down crying in Dean's arms.
The next day, Charlie says goodbye to Sam and Dean, who invite her to visit any time and look through the Bunker's archives. Charlie has learned from her experience and decides to let her mother go. At the hospital, Charlie signs forms to have her mother taken off of life-support and officially visits her for the first time, but before she lets her mother die, she reads The Hobbit to her one last time.