We examined (N = 281) the role of love styles and personality in people’s choice to engage in serious and/or various kinds of casual relationships (i.e., one-night stands, booty-calls, and friends with benefits) within the last year. Men were more eager than women were to engage in all types of casual relationships, however, love styles and personality traits were more important in accounting for this behavior. For instance, those with secure attitudes about love expressed an aversion to casual relationships; those with casual attitudes about relationships and who were dishonest reported involvement in various casual sex relationships; and conscientiousness was associated with engaging in serious romantic relationships but not one-night stands. The current study documents how an individual difference perspective can provide unique insights into people’s relationship behaviors to compliment work in social and evolutionary psychology.