Exercise is a vital component of human well-being, as regular physical activity is known to increase overall health, decrease psychological distress and depression, and decrease mortality risk from all causes. Despite its importance, 25% of Americans remain sedentary and a vast majority of the population does not meet the minimum activity guidelines set by the Centers for Disease Control. This research study analyzes the factors associated with a preference for exercise mode—group versus individual exercise regimens. Anticipated influencing factors include Self-Determination Theory (SDT), Big 5 personality traits, gender differences, occupation, and regular usage of a fitness tracker. It is hypothesized that males are more likely to participate in group exercise, while females are more likely to participate in individual exercise. Here we administered a five-part survey including a demographics section, exercise mode and frequency component, Ten-Item Personality Inventory (TIPI), Behavioral Regulation in Exercise Questionnaire (BREQ-3), and Exercise Motivation Inventory (EMI-2). Analyses determined no significance in the effects of sex on exercise preferences. Male-to-male analyses revealed a significant effect. The results will better inform future exercise studies regarding adherence factors. Future facilitation of exercise adherence will aid in designing physical activity engagement campaigns, tailored to individual populations, that emphasize enjoyable aspects of exercise.