This research focuses on the anthropology of gendered spaces and their connection with cultural aspects. Reviewing previous literature confirms that the cultural dynamics of gendered spaces in Jordan have not been widely researched, therefore exploring this subject will contribute to knowledge. Theorizing the interpretation of gender in urban spaces can shed light on gaps among culture and urban theories and identify some crucial concepts in the cultural dynamics of gendered spaces. This research aims at exploring the influence of cultural aspects on the behavior of middle-aged users in outdoor spaces. The research highlights the importance of understanding the cultural dynamics of gendered spaces. A comparative study is conducted to compare the landscape patterns in the old parts of Amman with the modern parts. A mixed methods approach is used to increase the accuracy of the research outcomes. The research findings confirm that understanding the users' behaviors, perceptions, and activities is important when planning and designing outdoor spaces. It also confirms the influence of cultural aspects on the behavior of individuals, especially women. The Research findings will affect government policy, professional practice, and the quality of the built environment; it will add great value to the field of gender-sensitive planning.