In designing for long-lasting outdoor activities, a space’s seating options and edge condition have been posited to have notable effects on staying behaviors. Danish architect Jan Gehl and American planner William H. Whyte concluded from their experiences observing public spaces that style of seating and relationship to the space’s edges have notable impacts on whether one chooses to sit down and how long they will stay once seated. Although these principles resonate with many, they have in fact received little careful and systematic evaluation. This study combined theories from prior informal observation of human preference regarding seating type and location and validated each with empirical evidence. Researchers conducted a naturalistic observation study over the course of eight days in March 2012, observing an opportunistic sample of 124 people. Results indicated that higher-quality seating type was associated with a longer duration of stay at a significant level. Duration of stay was not found to be impacted at a significant level by edge relationship, however, this may have been a result of a limited sample size. Opportunities for further research are outlined in hopes that we may continue to develop our understanding of these concepts, informing the design of livelier spaces and cities.