This note presents demonstrations of quadratic expressions that come about when particular problems are posed with respect to matchsticks that form regular triangles, squares, pentagons and so on. Usually when such "matchstick" problems are used as ways to foster algebraic thinking, the expressions for the number of matchstick quantities are linear and not quadratic. It will be shown that a pedagogy of "summing all the matchsticks" is central to the emergence of quadratic expressions. This pedagogy involves generational and transformational activities which are considered as some of the main activities of algebra. Key elements to these activities are processes such as recognizing and extending patterns, and specializing and generalizing particular functional relationships. Implications of these processes in terms of algebraic thinking are considered. (Contains 10 tables and 1 figure.)