Two investigations of relationship initiation were conducted to identify systematic differences in the selection of relationship partners. Specifically, it was hypothesized that the construct of self-monitoring would identify individuals who characteristically adopt distinctly different orientations when initiating dating relationships. In each of two interaction studies, low and high self-monitoring men chose a female partner for a date. Investigation 1 examined attentional differences in the initial information-seeking stage of relationship initiation in an open-field setting. Investigation 2 examined actual choices of dating partners where one type of desirable attribute in a partner had to be sacrificed in order to obtain another type of desirable attribute. Behavioral and self-report evidence revealed that in both the initial information-gathering stage and the actual choice of whom to date, low self-monitoring individuals paid a greater amount of attention to and placed greater weight on information about interior personal attributes than did high self-monitoring individuals; by contrast, high self-monitoring individuals paid more attention to and put greater weight on exterior physical appearance than did low self-monitoring individuals. Implications of these differences for the initiation, maintenance and dissolution of relationships were discussed.