Present day society is changing daily and the mobile device (laptop, PDA, smartphones, etc.) industry is striving to keep pace with these rapid changes. With the proliferation of numerous light weight devices along with the wide spread use of wireless local area networks (WLANs) in many public places we are more connected-on-the-go than ever. Recent studies have shown that there exist repetitive behavioral trends in the association pattern of groups in large WLANs. We believe that the predictability of WLAN users may affect socially aware networks in the future. To shed light on the changes and how protocols involving the mobility of users can change, we follow a systematic analysis methodology. First, we study the evolution of user mobility using extensive network traces collected over five years, using new mobility metrics that we define. In addition, we investigate a series of prediction methods in order to better predict WLAN users and study how changes in mobility influence the success rate of such predictors. We find that the more mobile a user becomes the less predictable he or she becomes. In our study we measure mobility by looking at the distinct number of access points(APs) visited by each user. The average number of distinct APs visited steadily grows at a rate of 3 APs each year over the 5 year period WLAN trace collected at Dartmouth College. The magnitude of correlation between the AP encounter ratio and prediction over all years is at a steady 0.5 to 0.6. Coupled with this we also show that the prediction success rate for 2005-2006 users are at an average 20% lower than that of the users of 2001-2002. We also investigated different granularities of success to see how these contribute to the overall predictability of mobile users. This study of user mobility and predictability paves the way for better understanding mobile users nowadays and gives us insight to potential evolution of network users' behavior in the future.