A 64 item Internet questionnaire was completed by 381 undergraduates at a large southeastern university to assess taking chances in romantic relationships. Almost three fourths (72%) self-identified as being a "person willing to take chances in my love relationship." Engaging in unprotected sex, involvement in a "friends with benefits" relationship, breaking up with a partner to explore alternatives and having sex before being ready were the most frequent risk taking behaviors. Both love and alcohol were identified as contexts for increasing one's likelihood of taking chances in romantic relationships--60% and 66% respectively. Being male, a senior, a "player," and Black were associated with higher frequencies of risk taking. Learning theory was used to explain the findings. Implications and limitations of the study are identified.