Although the quarterlife crisis is an increasingly recognized social phenomenon, much about this dynamic period in the life course and its impact on individuals remains unknown. How does the quarterlife transition inform individual expectations about future geographic mobility, and are these expectations salient across cultural boundaries? To explore questions such as these, I compare the expected future residential mobility of graduating college students in two different regions: Flanders, Belgium, which is characterized by the retention of young adults, and Upstate New York, which is characterized by immense out-migration of young adults. Interviews with young people in both regions provide a foundation of qualitative data, which is analyzed using a thematic framework rooted in sociological life course theory. Life-Span Development, Agency, Time and Place, Timing, and Linked Lives represent the five paradigmatic principles used to interpret the expectations of young adults in two different cultural contexts. The results reveal many similarities as well as some truly telling differences in the way individuals in different regions experience the quarterlife transition.