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Jill (Bill's birth name from before his transition)
Although Charlie Harper was a wild womanizer, he had some significant relationships in the past. Charlie and Jill dated for some time, and broke up. Jill apparently broke up with Charlie, which apparently saddened him. However, Jill 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 Jill, stating that he wanted to "see" him, and to meet him at a bar. Charlie decides to do so, as he enjoyed his time with Jill.
BillAt the bar, Charlie begins chatting with a man, coincidentally named Bill, about Jill. The audience soon figures out that that Bill and Jill are one in the same (evidenced by their laughter), and Bill finally reveals to Charlie that he is Jill, after the transition that changed his physical sex. Charlie is shocked to learn this, but nonetheless, takes Bill home with him. 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.
- Bill, in female form, never appears on-screen, and thus his pre-transition appearance is unknown.
- Charlie was so saddened by his break up with Jill, that he wept like a child and Berta had to carry him to bed for three days.