Empathy plays a fundamental role in building relationships. To foster close relationships and lasting engagements between humans and robots, empathy models can provide direct clues into how it can be done. In this study, we focus on capturing in a quantitative way indicators of early empathy realization between a human and a robot using a process that encompasses affective attachment, trust, expectations and reflecting on the other’s perspective within a set of collaborative strategies. We hypothesize that an active collaboration strategy is conducive to a more meaningful and purposeful engagement of realizing empathy between a human and a robot compared to a passive one. With a deliberate design, the interaction with the robot was presented as a maze game where a human and a robot must collaborate in order to reach the goal using two strategies: one maintaining control individually taking turns (passive strategy) and the other one where both must agree on their next move based on reflection and argumentation. Quantitative and qualitative analysis of the pilot study confirmed that a general sense of closeness with the robot was perceived when applying the active strategy. Regarding the specific indicators of empathy realization: (1) affective attachment, affective emulation was equally present throughout the experiment in both conditions, and thus, no conclusion could be reached; (2) trust, quantitative analysis partially supported the hypothesis that an active collaborative strategy will promote teamwork attitudes, where the human is open to the robot’s suggestions and to act as a teammate; and (3) regulating expectation, quantitative analysis confirmed that a collaborative strategy promoted a discovery process that regulates the subject’s expectation toward the robot. Overall, we can conclude that an active collaborative strategy impacts favorably the process of realizing empathy compared to a passive one. The results are compelling to move the design of this experiment forward into more comprehensive studies, ultimately leading to a path where we can clearly study engagements that reduce abandonment and disillusionment with the process of realizing empathy as the core design for active collaborative strategies.