Existing work on smokeless tobacco (SLT) often focuses on correlates and predictors of use, ignoring the social and cultural context surrounding initiation and continued use of SLT products. The current study takes a qualitative approach using guided focus groups to examine this unexplored context. The findings show that male SLT users gain social rewards from dipping with other men, and usage is initiated and continued in spite of known potential health consequences. For the men participating in this study SLT use was primarily initiated at social or athletic events with the encouragement of other men and continued for relational maintenance and bonding. Additionally, the men reported that the social rewards received from using SLT far outweighed any potential health consequences or negative social repercussions they might also experience. Implications for future research and health interventions targeting SLT use are discussed.