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Online dating sites require users to reveal information about themselves to find potential matches, yet users must also be wary of potential security and privacy threats. We conducted semi-structured interviews with 10 participants to better understand the various methods they employ to maintain their personal security and privacy while arranging to meet strangers in person. Specifically, we asked questions about how they validate the legitimacy of potential partners, how they safeguard their online information, and their overall experiences with dating sites. We found out that though users are familiar with most of the traits exhibited by scammers, they do not have sufficient security measures to protect themselves from being scammed. Users also have no principled means of balancing the need to share information with their need to stay safe. Our results suggest that better security and privacy mechanisms are needed to improve the online dating experience. Permission to freely reproduce all or part of this paper for noncommercial purposes is granted provided that copies bear this notice and the full citation on the first page. Reproduction for commercial purposes is strictly prohibited without the prior written consent of the Internet Society, the first-named author (for reproduction of an entire paper only), and the author's employer if the paper was prepared within the scope of employment.