Social engagement is important for health and well-being. There are very few observational measures available to assess social engagement of residents in nursing homes and assisted living facilities (ALFs) during activities. The objective of this quantitative research study was to document responses on the measure Fun and Social Engagement evaluation and to compare results obtained between nursing home residents and ALF residents participating in an in-person, group exercise program, Bingocize®. The majority of participants reported that they were “happy” and demonstrated positive behaviors such as playing Bingo, exercising, smiling, talking to other residents, and talking to staff and students. However, there was a significant difference according to setting with residents from ALFs demonstrating significantly higher social engagement than residents living in a nursing home. The most common negative behaviors observed included frowning and making a negative comment.