Jennifer Taylor's debut role in Two and a Half Men was in the pilot episode in 2003 where she played the role of Suzanne, a character that briefly appears at the grocery store where the chief characters Charlie and Jake are shopping. In the second season, she played the role of Tina, an ex-girlfriend of womanizer Charlie. She is the first ex-girlfriend Charlie has apologized to. Charlie proceeds to express his regret for not calling her earlier while Tina invites Charlie in and they sleep together which Tina refers to as a “fun apology.”
In 2007, she reappeared in the seventh season as Nina, a girl who falls for Charlie though the feeling is not mutual as Charlie just wants to sleep with her. But when Nina overhears Charlie referring to her as a random girl he picked up at the bar, she confesses that she actually believed in everything he said to her and storms out.
Since she was already quite familiar with the writers and producers of the show after reappearing as minor characters, when they saw fit to add a serious love interest for the womanizing character Charlie, Jennifer became their choice. Jennifer said of her lucky break, "Honestly, it is a dream come true...my perfect job, if given any job that I could have, would be to be on a Chuck Lorre-produced sitcom playing a strong, smart woman...that’s exactly what I got. I’m still blown away by that."
Her big break in the series came in 2008 when Chelsea became a major character. Fans of the series were shocked when the promiscuous Charlie confessed his love for Chelsea. She is noted for bringing a different side to Charlie.