Previous research has provided contradicting findings on whether valuing and pursuing happiness is beneficial or detrimental to one’s level of well-being. These contradicting findings might be resolved by considering these so-called Happiness Goal Orientations (HGO) as a multidimensional construct. The goals of this paper were (1) to present a new multidimensional scale to measure HGO and (2) to investigate whether the different dimensions of the scale are differentially related to well-being. Inspired by theories that distinguish between different dimensions of motivational systems and goal pursuit, we developed and validated the HGO Scale in four independent studies. The scale distinguishes two dimensions: Happiness-Related Strivings represent the propensity to move actively and persistently toward the desired level of happiness. Happiness-Related Concerns represent the propensity to worry about and to focus on threats to one’s level of happiness. Happiness-Related Strivings are associated with approach-related constructs, positivity, successful strategies to regulate one’s moods and emotions, endorsing a broad range of happiness definitions, and the intention to pursue different happiness definitions in everyday life. Happiness-Related Concerns are associated with avoidance-related constructs, anxiety, poor strategies to regulate one’s moods and emotions, defining happiness solely as the absence of negativity, and having no intentions to pursue happiness in everyday life. Happiness-Related Strivings are positively associated with well-being, whereas Happiness-Related Concerns are negatively associated with well-being. These differential associations with well-being demonstrate the importance of considering HGO as a multidimensional construct and that HGO can be both beneficial and detrimental to one’s level of well-being.