This study investigates the initial encounters of 30 Thai senior citizens and the four Thai musician-celebrity coaches in the blind auditions of "The Voice Senior Thailand season 1". The analysis was drawn from studies on compliments, politeness, and face work. The analysis found that both overt-oriented and covert-oriented compliments were used extensively when the coaches evaluated the senior contestants' vocal performances. The use of such compliments exhibits the shift from a distant relationship to a closer one. The prominent use of covert-oriented compliments as face-maintenance and face-enhancing strategies and as distance-minimization or imposition-mitigation strategies (Blum-Kulka, 2005) suggests rapport management between the four coaches and the senior contestants. Such interconnectedness of the multidirectional functions of compliments in Thai as well as face and politeness found in this study could exemplify how both younger and older generations of Thai people interact to form and shape a closer relationship in their first encounters in contemporary Thai language. This study could shed some lights on cross-cultural studies of complimenting behaviors and politeness in similar contexts or in other contexts related to younger and older generations in aging societies (e.g., workplace contexts or senior-education settings).