This research investigates significant moments in college students' drawn life stories in mathematics with the aim of examining implications for STEM engagement and potential reasons for gender-related differences in participation in mathematics intensive STEM fields. My research employs drawn life stories in mathematics specifically focused on students' experiences with mathematics to understand students' evolving relationships with mathematics, encompassing positive and negative experiences. My research extends previous work on "turning points" in students' mathematical experiences by introducing the concept of "key points" to more inclusively capture moments that intensify mathematical relationships. Employing mixed methods analysis of visual and written mathematical narratives combined with qualitative interviews, my research explores the effectiveness of allowing participants to visualize their mathematical journeys, and quantitatively assesses the impact of recurring themes in students' drawn life stories in mathematics. This research advances our understanding of factors that influence the nature of students' relationships with mathematics, and potentially inform strategies for enhancing STEM participation and gender inclusivity, using a unique approach in mathematical narrative research. Results from my research indicate that a wide variety of factors can have both positive and negative impacts on participants' mathematics identities. The most notable subthemes identified were "teachers" and "achievement" though a number of other themes were notable. Statistical significance tests showcased that while positive key points were more prevalent for male participants than female participants, the positive key points that existed tended to be more impactful for female participants than male participants. Additionally, relational themes tend to be more positively impactful for female participants than male participants; however, cognitively oriented themes tended to be more negatively impactful for female participants than male participants. Finally, my research developed an instrument known as "Drawn Life Stories in Mathematics" that has great potential both for future research and practice in allowing users to authentically reflect and share on their relationship with mathematics over the course of their lives. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]