Obesity is a chronic and growing disease defined by weighing 20% or more than the ideal, or having a body mass index (BMI) of 30 kg/m2 or more. While natural weight loss is available, many patients are choosing weight loss surgery (i.e., bariatric surgery) as an alternative to lose weight and reduce their risks for comorbidities such as diabetes, heart disease, and sleep apnea. Tools and resources for post-surgical support in the bariatric surgery community have been limited and, in the past, most tools and resources for weight loss have focused on non-surgical weight loss communities; as such, analysis methods for measuring success in this population have not been clearly developed and tested. This research proposes and evaluates analysis methods that may be used in such studies. These analysis methods are evaluated using data from the Weight and Exercise Lifestyle Support study at Baystate Medical Center in Springfield, MA. In this study, a group of participants (n = 6) approved for bariatric surgery were followed by the research team starting roughly one month before surgery through three months after surgery. Participants received pedometers and weight scales, and access to an online patient portal where they could review their physical activity levels, and receive support from others in the study and an exercise consultant. Data collected included pre- and post-study dietary and exercise self-efficacy levels, self-reported and objective physical activity measures, self-reported dietary adherence, device usage, and usability and satisfaction with the program. This research evaluates whether the proposed measures can help determine the presence and nature of the relationships between the aforementioned variables. If these measures prove to be useful, they can be used in future interventions that use technology to support post-surgical weight loss communities.