Research has shown that people select securely attached individuals as their first choice when asked to choose among secure or insecure partner prototypes. Despite this pattern, not everyone chooses a secure partner in real life. The goal of the reported studies was to examine factors that lead people to select insecure mates. Specifically, the roles of flattery, appearance, and status were assessed. In the first study, we found that flattery increased attraction to insecure partners. Study 2 showed that men preferred physical beauty over security. In Study 3, anxious women were attracted to high‐status insecure men. These findings help explain why people may sometimes end up with insecure partners despite their professed preference for secure companions.