People often view mathematics as abstract, cold, and irrelevant to real-life, and their school experiences influence such views. In this case study, we investigated the mathematics learning experiences of two women who participated in an afterschool girls STEM club 26 years ago. We explored their experiences in and out of school and how such experiences informed their images of mathematics. Data were collected from a survey, focus group interviews, and individual interviews. Using qualitative analysis, we learned that their school mathematics experiences influenced the participants' images of mathematics. The findings also revealed the participants' continuous and discontinuous learning experiences between school and out-of-school mathematics. This study suggests creating spaces to develop curricula that bridge the gap between school and out-of-school learning experiences. [For the complete proceedings, see ED630060.]