Online communication and self-expression through posting pictures have become a social norm. While most research’s focus has been on how these affected adolescents and anyone bracketed in generation Z, those born between 1995 and 2015, this paper will be looking at the impact of social media and selfie culture on those in generation Y, better known as Millennials, born between 1980 and 1994. This subset of social media users was not born with access to camera phones or social media, yet they have adopted it for both professional and personal interactions. This study aimed to investigate whether individualism and collectivism in the west and east respectively can impact the results, to understand what motivates the millennials to take selfies, to investigate how millennials perceive their selfie habits, whether the millennials who take selfies exhibit similar narcissistic traits, and to find out if and how selfies impact the lives and relationships of the millennials. This research focuses on qualitative, semi-structured interviews done with a selection of professionals aged between 23 and 39 years, capturing insight from the oldest Millennials to the youngest. The findings revealed that there were several areas concerning the millennials’ view of expression through selfies. Many millennials believed taking and posting selfies was negative behavior and judged others for doing so however they partook in the same behavior. The motivations for taking selfies were predominantly similar; memories and keeping family and friends informed. However, a millennial’s definition of a selfie did differ. Within a conclusion in this study is language surrounding selfie culture is predominantly negative; this includes language used by people who take selfies. The millennials’ actions could be viewed as hypocritical as they say the pictures posted on social media are fake and not a true representation of popularity yet they still take part in this behavior. Understanding the millennials’ expression through selfies is key to understanding how they view themselves and the world around them. Even if a millennial fabricates their life through editing a selfie this in itself offers an insight into how they deal with life. It may be prudent to revisit some language used to describe the use of social media.