The goal of this research was to better understand the knowledge, preparedness, and comfort level of single fathers with daughters regarding menarche and menstruation. To achieve this goal, a Google Forms survey was distributed using social media, and the data from this survey were analyzed using chi-squared tests and a regression model. Of 446 responses, 387 were included for analysis. It was found that comfort discussing the menstrual cycle significantly positively correlated with knowing their daughters’ menarcheal status and self-rated knowledge about the menstrual cycle, and negatively correlated with selecting parents as a responsible party for menstrual education. Knowledge level was significantly positively correlated with the number of subjects related to the menstrual cycle participants selected as being knowledgeable about, but was not significantly correlated with knowing menarcheal status or considering parents a responsible party for menstrual education. Considering parents a responsible party was also not correlated with having talked to their daughter about the menstrual cycle. Additionally, there was some evidence that comfort discussing menstruation is negatively correlated to age. The information gained from this study indicates that it would be beneficial to increase single fathers’ knowledge and comfort discussing the menstrual cycle in order to ensure the menstrual health of their daughters.