When asked directly, most young people show a relatively low level of political interest. Despite this, Scandinavian youth exhibit reasonable voter turnout compared to most countries. In this study of young Danish first-time voters, we elaborate the peculiarities of their political reasoning and orientations. We approach our analysis on the basis of rationalistic theories of voting as well as the use of heuristics in voting decisions. We also build on the theory of political socialization and voters’ loyalties to family in their decisions. Methodologically, we use the oral stories of ten students from upper secondary school on how they arrived at a voting decision. The article elaborates the decisions, paradoxes, and ambivalences which these young people display in the process of casting a vote. We claim that the individuals in our study handled this discrepancy by the active use of different strategies. Students particularly tried to simplify their choice of party by focusing on one or two important issues. They used strategic rationalism as well as value rationalism and idealistic approaches to decision-making. Above all, students used cognitive heuristics extensively. Generally, first-time voters often find themself in complex decisions facing an overload of information and sometimes trapped between loyalties, particularly to their families, but rarely to their social class. Based on our findings, we suggest that teachers should sometimes provide meaningful heuristics to guide students’ complex choices as first-time voters.