Green roofs are shifting expectations of where urbanites encounter ‘nature’ in the city, particularly because they do not carry the symbolism of more traditional forms of urban nature such as parks. Though often implemented for ecological reasons, green roofs are drawing increasing research interest into how people think and feel about them as examples of urban nature. This chapter uses an in-depth case study to examine the values, expectations, and assumptions underlying office workers’ perceptions of green roofs, place, and aesthetics in Toronto and Chicago. Specifically, this chapter examines what we can learn about the human relationship to urban nature from this case study, how this research links to nature, health, and sense of place research, and how Toronto and Chicago approached policy and implementation. This chapter also compares the results of using a phenomenological methodology and survey responses from the same population. Results from this case study imply that green roofs with a ‘wild’ ecological aesthetic may in fact increase acceptance of ‘wilder’ urban greening projects by providing cues to care, references to regional habitat, and childhood memories. The case study also indicates that methods matter, with differences found between quantitative survey responses and more ‘felt’, or lived experience, responses to urban greening evident in interview responses.