We examine the moderating role of friendship and school network characteristics in relationships between 1) youths' friends smoking behavior and youths' own generalized expectancies regarding risk and future orientation and 2) generalized expectancies of youths' friends and youths' own generalized expectancies. We then relate these constructs to smoking. Using a longitudinal sample from the National Longitudinal Study of Adolescent Health (N = 15,142), the relationship between friends' generalized expectancies and youths' expectancies is stronger for those more central in the network, with more reachability, or stronger network ties, and weaker for those with denser friendship networks. Risk expectancies exhibited an inverted U shaped relationship with smoking at the next time point, whereas future orientation expectancies displayed a nonlinear accelerating negative relationship. There was also a feedback effect in which smoking behavior led to higher risk expectancies and lower future orientation expectancies in instrumental variable analyses.