The political strategies used to attract Taiwanese Millennials is a puzzling topic. This article analyses the strategies the two main political parties have implemented in recent years to do so. In the literature on youth attitudes in Western democracies, politics is described as “boring,” a “big turn-off,” and a “killjoy.” I examine to what degree these theoretical terms can help define the youth’s perception of politics and I describe the youth-led demonstrations that have taken place. Using primary sources, this analysis unfolds the objectives, successes, and failures of the youth wings of two political parties founded in early 2006. The 2008 and 2012 presidential campaigns are considered in relation to the theme of youth engagement. A key event in recent years was the March–April 2014 Sunflower Student Movement. The impact of this event and youth politics leading up to the 2016 presidential and legislative elections is discussed.