The artificial intelligence (AI) revolution has arrived, as AI systems are increasingly being integrated across organizational functions into the work lives of employees. This coupling of employees and machines fundamentally alters the work-related interactions to which employees are accustomed, as employees find themselves increasingly interacting with, and relying on, AI systems instead of human coworkers. This increased coupling of employees and AI portends a shift toward more of an “asocial system,” wherein people may feel socially disconnected at work. Drawing upon the social affiliation model, we develop a model delineating both adaptive and maladaptive consequences of this situation. Specifically, we theorize that the more employees interact with AI in the pursuit of work goals, the more they experience a need for social affiliation (adaptive)—which may contribute to more helping behavior toward coworkers at work—as well as a feeling of loneliness (maladaptive), which then further impair employee well-being after work (i.e., more insomnia and alcohol consumption). In addition, we submit that these effects should be especially pronounced among employees with higher levels of attachment anxiety. Results across four studies (N = 794) with mixed methodologies (i.e., survey study, field experiment, and simulation study; Studies 1–4) with employees from four different regions (i.e., Taiwan, Indonesia, United States, and Malaysia) generally support our hypotheses.