The internet provides the means through which a “self-activating terrorist” may first self-radicalize through some imaginary or sympathetic connection with an organized terrorist network. Additionally, the internet allows such a self-activating terrorist to move into the stage of radical violent action. The internet serves both functions by providing the lone wolf with not only a rhetorical medium for self-justification and communication through the use of “monster talk” and its converse, the rhetoric about the “good citizen,” but it is also a source for relatively inexpensive and more unpredictable technologies of mass destruction. Crucial to this analysis is the distinction between radicalization of thought and radicalization of action, as a theoretical rhetoric of radicalization does not automatically convert into a rhetoric of radical action unless there are catalysts at work. The internet, as well as imagined relations cemented by the rhetorics of “jihadi cool” or “jihadi chic,” function as these crucial catalysts, galvanizing monster talk into monstrous action. The article focuses specifically on the case of self-activating terrorist Colleen LaRose to analyze how different factors—mental, psychological, social, and economic—interact with imaginative elements, such as surrogate father-mentor-lover relations for LaRose, and contribute to the formation of a self-activating terrorist, and what ultimately motivates and galvanizes her to move from a rhetoric of radical talk to a rhetoric of radical action, using Silber and Bhatt’s model of radicalization as an initial heuristic. In the case of Colleen LaRose, the romance of “jihadi chic” or “jihadi cool” (the converse of the rhetoric of the monstrous “infidel” or “lone wolf terrorist”) was an essential factor to her self-radicalization. It is this imagined status of “jihadi chic” or “jihadi cool” (that nevertheless must somehow have a look of “reality” or “authenticity” and command a response from its audience) that continues to be a crucial component of the success of recruitment strategies of radical jihadi groups, such as ISIS.