Consistently, there are more creative and fast paced forms of entertainment to help people escape, cope, or adjust to the stress of life. Whether finding it through substance, technology, or a variety of other methods, individuals are becoming more daring, tech savvy and tech dependent. Two areas that have seen explosive growth exists in the world of daily fantasy sports contests and the emergence of legalized sports gambling. With the advent and expansion of these skill-based forms of entertainment, individuals have access to information and opportunities to wager 24 / 7. This workshop will explore the psychological aspects and gambling-like mechanics common to daily fantasy sports contests while looking at emerging trends and future considerations in sports gambling.