Those who are rejection sensitive anxiously expect and readily perceive rejection. Rejection sensitivity is hypothesized to predict behavior; however, this link may be more evident in some contexts than others. The current study examined the link between rejection sensitivity and condom use. Australian young adults in romantic (n = 649, 70% female) and casual (n = 144, 76.2% female) relationship contexts completed measures on rejection sensitivity, condom use preferences, and condom use. Regression analysis showed that rejection sensitivity predicted condom use when participants’ condom use preferences were at odds with those they thought their partner held. Specifically, highly rejection-sensitive individuals who preferred more frequent condom use reported using condoms less often, if that was what they thought their partners wanted. The results lend support to the model of rejection sensitivity in that individuals comply more with their perceived partner’s preferences if they are more rejection-sensitive. The results also highlight the need to take the situational context into consideration when examining links between personality dispositions and behavior.