Holiday healthfulness conversations are dominated by overindulgence of consumption and then, largely in reference to resolutions to do better, physical activity, and exercise aspirations. Consistency was found in self-reported agreement with a series of holiday healthfulness statements, across time, holidays (Thanksgiving versus Christmas), and samples of respondents. The largest proportion of respondents displaying social desirability bias (SDB) were found in response to two statements, namely “I will consume more alcohol during the holiday season than at other times of the year” at (63–66%) and “I make it a New Year’s Resolution to lose weight” (60–63%). Cheap talk was tested as a mechanism to reduce SDB in holiday healthfulness reporting, but showed only limited efficacy compared to the control group surveyed simultaneously. Nonetheless, the consistency across time in reporting and SDB are notable in both self-reporting of health-related data and in studying a unique consumption period around the holidays. Healthcare providers and researchers alike seek to improve the accuracy of self-reported data, making understanding of biases in reporting on sensitive topics, such as weight gain and eating over the holiday season, of particular interest.