Variability stands in the heart of statistics theory and practice. Concepts and judgments involved in comparing groups have been found to be a productive vehicle for motivating learners to reason statistically and are critical for building the intuitive foundation for inferential reasoning. The focus in this paper is on the emergence of beginners’ reasoning about variation in a comparing distributions situation during their extended encounters with an Exploratory Data Analysis (EDA) curriculum in a technological environment. The current case study is offered as a contribution to understanding the process of constructing meanings and appreciation for variability within a distribution and between distributions and the mechanisms involved therein. It concentrates on the detailed qualitative analysis of the ways by which two seventh grade students started to develop views (and tools to support them) of variability in comparing groups using various statistical representations. Learning statistics is conceived as cognitive development and socialization processes into the culture and values of “doing statistics” (enculturation). In the light of the analysis, a description of what it may mean to begin reasoning about variability in comparing distributions of equal size is proposed, and implications are drawn.