African American men have high rates of chronic disease morbidity and mortality associated with their low rates of fruit and vegetable consumption. In an effort to inform tailored behavioral interventions for this demographic, we sought to assess if men with healthier eating practices viewed their environment differently than those who ate less healthy. We segmented participants into high/low healthy eating categories based on the daily fruit and vegetable serving recommendations from the U.S. Department of Agriculture to determine if differences among environmental and social barriers were associated with different healthy eating patterns. We found key differences between men who consumed the recommended amount of fruits and vegetables (five or more servings/day, high healthy eating) and men who did not (low healthy eating). Men who consumed recommended levels of fruits and vegetables found eating healthy to be easy, and they described how they were able to overcome barriers such as the cost of healthy food, their limited knowledge of nutrition guidelines, and their lack of willpower to make healthier food choices. Men with healthier eating practices also identified individuals, plans, and resources they used or could use to help them have healthier eating practices. Conversely, men who were not eating recommended levels of fruits and vegetables also found eating healthy to be easy; however, they identified barriers limiting their access and did not articulate strategies to overcome these perceived barriers. Many of these men also indicated that they did not have social support to help them engage in healthier eating practices. These findings highlight the need to understand how African American men’s conceptualization of environmental resources and social supports relate to their eating practices.