Research on workplace drinking has primarily focused on its detrimental consequences, overlooking why the phenomenon has continued to proliferate in the business world. My research offers a potential explanation by suggesting drinking’s potential functional role in building trust and bringing relational benefits. Drawing on uncertainty reduction theory, I predict that at the initial stage of the socialization process, newcomers’ high levels of social drinking behaviors with their supervisors are positively associated with supervisory trust in the newcomers. Moreover, during the dynamic socialization process, I predict that increases in newcomer social drinking over time (i.e., positive trajectories of newcomer social drinking) are associated with decreases in supervisory trust over time (i.e., negative trajectories of supervisory trust). In turn, I predict that high levels of initial supervisory trust and increases in supervisory trust will benefit the newcomers with relational support in the form of supervisor helping and reward recommendations. A multisource, multi-wave longitudinal field study provided general support for my hypothesized model. My research adds nuance to the discussion of workplace drinking activities and contributes to the literature by demonstrating how social drinking between newcomers and supervisors can lead to trust development at the initial stage of socialization process but hurt the trust relationship if increasing to drink over time, which further negatively affects the relational benefits.