Dark chocolate is not the most popular chocolate; the higher concentration in antioxidants pays tribute to the increment in bitterness. The caloric density of dark chocolate is potentially lower but has a large variability according to recipes and ingredients. Nevertheless, in the last decade, the interest in dark chocolate as a potential functional food has constantly increased. In this review, we present the nutritional composition, factors influencing the bioavailability, and health outcomes of dark chocolate intake. We have extracted pro- and counter-arguments to illustrate these effects from both experimental and clinical studies in an attempt to solve the dilemma. The antioxidative and anti-inflammatory abilities, the cardiovascular and metabolic effects, and influences on central neural functions were selected to substantiate the main positive consequences. Beside the caloric density, we have included reports placing responsibility on chocolate as a migraine trigger or as an inducer of the gastroesophagial reflux in the negative effects section. Despite an extensive literature review, there are not large enough studies specifically dedicated to dark chocolate that took into consideration possible confounders on the health-related effects. Therefore, a definite answer on our initial question is, currently, not available.