Two and a Half Men Wiki
Two and a Half Men Wiki

Bill Shrader (born Jill Shrader) is a transgender man who, when he was closeted and in denial about his gender, was an ex-girlfriend of Charlie Harper.

Backstory[]

Although Charlie Harper was a wild womanizer, he had some significant relationships in the past. Charlie and Bill dated for some time when Bill was in denial about his transness and believed he was a woman, before the two broke up. Bill apparently broke up with Charlie, which apparently saddened Charlie. However, Bill was important enough to Charlie that he was able to recall both him and the relationship they shared. Five years later, Charlie received an email from Bill. The email was sent under Bill’s deadname (a trans person’s birth name, not their chosen one), and Charlie is still unaware that Bill transitioned, so he refers to him with his deadname and she/her pronouns, The email states that Bill wanted to "see" him, and to meet him at a bar. Charlie decides to do so, as he enjoyed his time with Bill.

Bill[]

At the bar, Charlie begins chatting with a man, coincidentally named Bill, about his ex girlfriend, who is actually Bill pre-transition. The audience soon figures out that Bill and the ex-girlfriend are one in the same, and Bill finally reveals to Charlie that he is the ex-girlfriend and is now living as a man after coming to terms with his gender identity and transitioning. Charlie is shocked to learn this, but nonetheless, takes Bill home with him to talk. Bill meets Charlie's mother, Evelyn. Charlie later learns that Bill and Evelyn have entered a relationship, the first one of Evelyn's that is not primarily sexual, but motivated by Bill's interesting nature, knowledge of "womanly" topics, and many pairs of shoes that fit Evelyn. Charlie notes the irony of the situation is that he slept with the man who is currently sleeping with his mother, and jokes that he intends to title his autobiography something along those lines. Alan and Berta later learned of Bill's past being shocked and amused respectively. Later, Charlie told Bill to tell his mother the truth of his past.

Much later, Bill told Evelyn the truth of his past, his relationship with Charlie, and she fainted from shock. This was witnessed by Charlie, Alan, and an amused Berta.

Despite that, she came to terms with it and the relationship continued.

Ht2

Evelyn presenting Bill, from "An Old Flame With A New Wick".

Trivia[]

  • Bill, pre-transition, never appears on-screen, and thus his pre-transition appearance is unknown.
  • Bill never met anyone in the Harper family during his time as Jill and met them years later.
  • Charlie was so saddened by his break up with Bill, that he wept like a child and Berta had to carry him to bed for three days.
  • In the later seasons, Bill is never heard from again and he probably doesn't know that Charlie died.