Abstract The longitudinal associations between Facebook use and well-being have received limited exploration with mixed results. We argue that the transition pattern of an individual’s social grooming style based on five social grooming behaviors at different times—referred to as the social grooming transition pattern—is the key to exploring this issue. Based on the social grooming style framework, we employed latent transition analysis through a nationally representative, three-year panel survey (N = 710) in Taiwan. We found that active users remained active in social grooming behavior and had options to shift, and inactive users largely remained inactive in terms of Facebook social grooming style. The results indicated that persistent social image managers gained the most social capital and well-being, greater than persistent social butterflies and those who transitioned from image managers to social butterflies, indicating that adopting strategic social grooming styles in the long-term delivered the best social outcomes. Lay Summary The long-term interaction between Facebook use and well-being has received limited attention with mixed results. One way to examine this is to study changes in the way that we “groom” one another in Facebook. That is, how we socially interact with others by discussing different topics with various styles and strategies. Based on the social grooming framework, we provide the first study employing latent transition analysis (i.e., to track how people change or maintain their social grooming style across time) to examine this issue using a nationally representative, three-year panel survey from Taiwan. Our study shows that most people maintain a stable user style over time. However, some become less active (e.g., they become “maintainers” or “lurkers”). Thus, the majority of Taiwanese users often do not create their own postings, but rather comment on, or simply view, the content of other Facebook users. By contrast, users who actively groom (e.g., those who are persistent “social butterflies” or “image managers”) continue to create online posts. Our analysis shows that users who are highly social benefit from greater bridging social capital. However, the strategically active social groomer is the winner as they benefit by gaining greater bridging social capital, social connectedness, and social life satisfaction.