This study utilizes the autoethnographic method of research to examine and reflect on dating and disability while focusing on themes of sexuality, body image, and masculinity. Dating with a disability is sometimes deemed controversial or even inappropriate, and there is a slight societal awkwardness and discomfort when the topic arises. This research intends to act as a first step in breaking this awkwardness and shall act as a catalyst in helping to dismantle ableist attitudes surrounding in-person/online dating. Since research is rarely done on such an intimate field as dating, this study aims to give a unique insight into the struggles and successes of the joint topics of dating and disability. Through this autoethnography readers shall have the opportunity to reflect on their own dating experiences and will be given the chance to challenge their own ableist attitudes. Lastly, I hope that this study inspires more research into dating and disability, particularly research focused on themes of sexuality, masculinity, and body image.