The authors argue that felt insecurity in a partner's positive regard and caring stems from a specifically dyadic perception--the perception that a partner is out of one's league. A cross-sectional sample of dating couples revealed that people with low self-esteem feel inferior to their partner and that such feelings of relative inferiority undermine felt security in the partner's regard. Three experiments examined the consequences of reducing such perceived discrepancies by pointing to either strengths in the self or flaws in the partner. Low, but not high, self-esteem participants reacted to new strengths in the self or faults in the partner by reporting greater felt security in their specific partner's positive regard and commitment and more positive, general feelings about their own interpersonal worth. Thus, putting the partner more within the psychological grasp of low self-esteem people may effectively increase felt security in the partner's regard.