The objective was to further elucidate and understand the widespread opposition to the Affordable Care Act (ACA). From April–July 2016, authors conducted open-ended, unstructured conversations with people they met as they rode their bicycles across the US, as a convenience sample. Conversations, open-ended and lasting 15–30 minutes, were maintained by the authors via indirect prompting and silent probes. Demographics were obtained as was the sentiment toward the ACA for the 116 individuals. The majority (54%) were negative toward the ACA. Conversations were categorized into four themes: 1) Obama Care has increased the cost of health insurance, 2) government should not tell people what to do, 3) uncertainty as to who is responsible for the negative outcomes of Obama Care, and 4) lack of concern for fellow citizens. Our face to face conversations indicate that this opposition may be due to the fact that many Americans have experienced an increase in the cost of insurance either by increased premiums or deductibles. They blame this increase in the cost of health insurance on the ACA, Obama, the government, or on insurance companies.