The digital generation represented by youth through college students in modern society holds much of their personal identity via the web. Social media and networking websites enable these individuals to disclose different levels of their identities with privacy setting options. This may or may not allow such information to be disclosed, but our focus is on the individual’s mentality of how much information they are disclosing online. Following the research of Adam Joinson (2001) regarding greater amounts of disclosure via computer-mediated-communication versus face-to-face communication, we were inspired to conduct a study of our own. We examined the Facebook community, paying close attention to the relationship between privacy settings and the likelihood of adding ‘new friends,’ specifically friends that are “unknown”. In order to be consistent we created Grace Lee, a fictional Northeastern student, with a Facebook comprised of a photograph from an online image, a variety of likes and interests hoping to attract an eclectic group of Facebook friends. Friend requests were made on the basis of researcher’s close friends, acquaintances and unknown individuals. We hypothesized individuals with greater privacy settings would be more reluctant to friend someone they do not know personally. Prior to friending each individual privacy settings were inspected. Once the study was conducted we found there was no significant difference between privacy settings of those who did add Grace Lee and those who did not, disproving our position. However, we did find that friend acceptance was more likely with the presence of mutual friends.