The consumption of phenol-rich foods is limited by their prominent bitterness and astringency. This issue has been addressed by adding sweet tastes, which suppress bitterness, but this is not a complete solution since individuals also differ in their preference for sweetness. In this study, we aimed at identifying groups of consumers differing in sweetness optima and sensory-liking patterns. To this end, increasing concentrations of sucrose were added to a chocolate pudding base. This allowed us to (1) investigate if individual differences in sensory responses are associated with different sweet liking optima in a product context, (2) define the psychological and oro-sensory profile of sweet liker phenotypes derived using a product context, and (3) assess if individuals differing in sweet liking optima differ also in consumption and liking of phenol-rich foods and beverages as a function of their sensory properties (e.g., sweeter vs. more bitter and astringent products). Individuals (1208; 58.4% women, 18–69 years) were characterised for demographics, responsiveness to 6-n-propylthiouracil (PROP), personality traits and attitudes toward foods. Three clusters were identified based on correlations between sensory responses (sweetness, bitterness and astringency) and liking of the samples: liking was positively related to sweetness and negatively to bitterness and astringency in High and Moderate Sweet Likers, and the opposite in Inverted U-Shaped. Differences between clusters were found in age, gender and personality. Furthermore, the Inverted-U Shaped cluster was found to have overall healthier food behaviours and preferences, with higher liking and consumption of phenol-rich vegetables and beverages without added sugar. These findings point out the importance of identifying the individual sensory-liking patterns in order to develop more effective strategies to promote the acceptability of healthy phenol-rich foods.