Baumeister, Tice, and Hutton proposed that individuals with low self-esteem (LSEs) adopt a more cautious, self-protective self-presentational style than individuals with high self-esteem (HSEs). The authors predicted that LSEs’ self-protectiveness leads them to be less expressive—less revealing of their thoughts and feelings—with others than HSEs, and that this self-esteem difference is mediated by their perceptions of the interaction partner’s regard for them. Two correlational studies supported these predictions (Studies 1 and 2). Moreover, LSEs became more expressive when their perceived regard was experimentally heightened—when they imagined speaking to someone who was unconditionally accepting rather than judgmental (Study 3) and when their perceptions of regard were increased through Marigold, Holmes, and Ross’s compliment-reframing task (Study 4). These findings suggest that LSEs’ expressiveness can be heightened through interventions that reduce their concerns about social acceptance.