This chapter employs irony as a tool to make clearer the workings of one form of the e-politics of food, namely, the structural food oppression linked to the weight and shape of the female body. The authors argue that the e-politics of the weight and shape of the female body is one of the most important incarnations of the e-politics of food and one of the most vigorously contested. This chapter examines many forms of public discourse and e-politics, from Bing to Tumblr, from Huffington Post to the Mirror (UK), from TV news in Lacrosse, Wisconsin to The Times of India, from the documentary film Killing Us Softly to the book You Are What You Eat, and from WebMD to Twitter, in the end, with a central focus on Rachel Frederickson on the TV show, The Biggest Loser. The critical rhetorical analysis finds some support for the Women Can't Win thesis. Women are in a Catch-22 situation, trapped between fat-shaming and skinny-shaming.