In this paper we address a new problem of predicting affect and well-being scales in a real-world setting of heterogeneous, longitudinal and non-synchronous textual as well as non-linguistic data that can be harvested from on-line media and mobile phones. We describe the method for collecting the heterogeneous longitudinal data, how features are extracted to address missing information and differences in temporal alignment, and how the latter are combined to yield promising predictions of affect and well-being on the basis of widely used psychological scales. We achieve a coefficient of determination (R²) of 0.71-0.76 and a correlation coefficient of 0.68-0.87 which is higher than the state-of-the art in equivalent multi-modal tasks for affect.