Anthocyanins are ubiquitous pigments in nature and common in the diet; they exhibit large chemical diversity, which affects the colors they express, their stability, and their bioactive properties. Anthocyanins are typically first encountered in the oral cavity during ingestion where metabolism and absorption begins. Within 5 min of contact with oral tissues, they have been detected in plasma. The absorption and metabolism of anthocyanins in the body, in general, has not been well-characterized and information about their activities in the oral cavity is even further limited. Several factors that affect the stability, reactivity, and bioavailability of the pigments in the mouth are summarized, including their natural structure, the oral pH, components of saliva including inorganic compounds and proteins, and the oral microbiota. Anthocyanin contact with tissue alone may be sufficient to provide localized health-promoting benefits; however, transportation and absorption are necessary for systemic health effects. The current knowledge about absorption of anthocyanins in the oral cavity is also summarized, regarding means of application and necessary enzymes and transporters. Commonalities between oral and gastrointestinal absorption and metabolism suggest that similar enzymes and transporter proteins may be used in tissues of both sites. Further understanding of anthocyanin metabolism in the mouth may provide insights into their behavior in other sites in the body.