The major thing that jumped out at me when I saw the still shot of Mrs. DiLarentis and her 3 children was the color of one of the boy’s shoestrings. One has blue, while the other has pink. They are dressed very similarly with the shoestring colors being the only major difference.
That makes me think that the theories that I have read about Charles identifying as a female are true.
Ok, so Mrs. D has 2 boys, how I don’t know. (Whether or not they are twins is still up for debate in my mind) Early on Charles knows that he is a female trapped in a male’s body and expresses his self to his parents. Mrs. D supports him, hence the pink shoe laces. However, Mr. D doesn’t and Mrs. D has to support Charles behind her husband’s back, as shown when she purchased two dresses (they could be the same dress, but not the same size) and made Ali swear that she wouldn’t mention them to her father. I believe that Charles was sent to Radley way before the scene with the dresses ever happened (since Ali seemingly has no recollection of having another brother).
So, Charles’ parents have him committed due to what Mr. D feels is him having mental issues. Not too many people remember Charles , however there is one person in the neighborhood that does…Toby’s mom. She has seen the boy, maybe even interacted with the boy and then one day, the boy is gone. She inquires about his disappearance and is made to feel crazy. That coupled with other issues in her life lead to feelings of self-doubt and possible guilt over not being able to help the boy she once knew. This eventually gets her committed to Radley where she meets Charles again. Now, before Toby’s mom was ever committed, Charles was there and he made a friend, Bethany.
Charles was immediately drawn to Bethany because she reminded him so much of his little sister Ali. Charles, Bethany and Mrs. Cavanaugh form a little family. Charles and Marion bond over their dislike of the Dilarentis’ and Bethany just appreciating being with them. Mrs. D learns of this “family” and knows she needs to get Charles away from Mrs. C, she does this by showering Charles and Bethany with gifts and trips (this is how Bethany gets to the horse farm). This does not work on Charles however, Bethany is taken in and begins to spend time with Mrs. D and eventually Ali. Mrs. D brainwashes Bethany on just how evil Mrs. C (and possibly Charles) is.
Bethany who is in Radley for good reason believes her, and this causes her to push Mrs. C off of the roof. This causes Charles to have his first real mental break in his own already fragile mind. He is able to convince Bethany that Mrs. D and Ali are the enemy and that they must be retaliated against. They hatch a plan to get out of Radley and practice breaking in and out terrorizing Ali for fun (the first Halloween).
The night everything in the world happened, Mrs. D got the phone call that the two had broken out and this time someone noticed. She is alarmed and tries to warn Ali. She gets there and sees Ali in the grave and knows that it was Charles who hurt her. In order to protect one child, she buries Ali.
As we know Ali is saved and the hole becomes empty. Charles is upset and enraged that his plan is not going well and he goes for who he believes is Ali again. This time instead, he hit Bethany and runs back to Radley in fear and in emotional pain. Melissa sees who she thinks is Ali in the grave and buries her to protect Spencer and in the meantime Ali is on her way out of town. Charles is devastated and remains inactive until a new resident of Radley is admitted. He then steals the game from Mona.