In this chapter, the adaptive interplay between bonding by homophily and adaptive mirroring by Hebbian learning within the context of joint decision-making is explored by second-order adaptive network modeling. Second-order adaptive mechanisms were applied to capture the adaptive dynamic interplay between these processes. Several simulation experiments were conducted across different scenarios to investigate the influence of various characteristics on formation and maintenance of social bonds, learning, and decision-making. The obtained model may be applied for computational analysis of collaborative human-bot interactions in order to jointly make decisions while bonding and adapting.