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Online search and brokering (OSB) is the phenomenon in which youth search for information for their immigrant families on the Internet. Few studies exist on reflecting on the past as youth conduct OSB from childhood to adolescence to young adulthood. We conducted a retrospective study using semi-structured interviews of 27 young adults (ages 19 - 24) to examine their experience and perceptions of OSB over time (primary schooling, secondary schooling, undergraduate). We found that although all the interviewees shared a common experience of being an online searcher and information broker for their immigrant families, their stories exist on various dimensions which are constantly shifting and changing over time, as ecological factors influence searching behaviors. We discuss how the results from our study can serve as future references for researchers doing work in search research and designers who are currently working on improving design tools for searching.