Jennifer Taylor (Chelsea)
Jennifer Taylor made history when her character, Chelsea, was the first person Charlie proclaimed his love to. He tried to play it off as if it were some huge joke, but he later on admits that he was for real. It was such a huge surprise to fans because nobody could have foreseen Charlie having feelings toward a woman with whom he had a one-night stand.
The two had a pretty serious relationship, and true to Charlie fashion, he proposed to Chelsea to get her to say that she loved him back. Chelsea wound up dating Alan’s attorney, and Charlie got it on with Chelsea’s best friend.