This paper aims to show how people use and understand metaphorical language in conversational discourse. Specifically, I examine how metaphorical language has the potential to be either effective or ineffective in its usage, and how they are bound to the contextual environment of the conversation. This particular setting is a conversation between a researcher and a participant involved in a therapeutic program. Metaphorical language is shown to be helpful for understanding difficult subjects; however, I found most metaphorical occurrences ineffective in meaning-making. Often these ineffective metaphors are elaborated or repeated throughout the discourse event, creating problems with cohesion and understanding. Metaphor use in conversation is an effective rhetorical tool for creating meaning, but it is also a problematic device when it comes to aligning participants' conversational goal.