It is known that obesity and hypertension have a relationship with one another. Often, obesity is thought to directly cause hypertension, with a list of mechanisms commonly cited. This, however, does not do the relationship justice. Not only can the directionality of the relationship be flipped, but the mechanisms may be misattributed confounders, themselves. Beyond this, some argue that the results of trials using glucagon-like-peptide-1 receptor agonist (GLP1R) medications suggest a causal relationship between obesity and hypertension, but this will be debunked. The relationship is far from linear, and mainstream literature often excludes key confounders that will be discussed in this article including food insecurity, mental health, socioeconomic status (SES), and weight stigma and discrimination. The factors used to measure the risk of hypertension as well as the measurements of hypertension, itself, need to be reexamined. For instance, there may be a high amount of “false positives” among the diagnosed. Finally, current research needs to be critically evaluated for forms of weight centrism and weight bias, deciphering improper assumptions from true, evidence-based science.