CONTEXT: In urban areas of the United States, syphilis is a major public health issue for men who have sex with men, despite widespread efforts to curtail a growing epidemic; repeated infections are not uncommon in this population. The ways that men who have sex with men experience and conceptualize syphilis, and how their attitudes and beliefs impact their risk for infection, are poorly understood. METHODS: In-depth interviews were conducted in 2010-2011 with 19 Los Angeles County men aged 21-54 who reported having male sex partners and had had two or more early syphilis infections within the previous five years. Interview transcripts were analyzed inductively to uncover themes. RESULTS: Participants had considerable knowledge about syphilis symptoms, transmission and consequences, and most felt that syphilis was a highly stigmatized disease. They had had 2-5 infections in the past five years, and the majority believed they were at risk for another infection because of their sexual risk behaviors. Many had a sense of fatalism about being infected again, and some expressed that this possibility was an acceptable part of being sexually active. Concern about syphilis often decreased as men experienced more infections. Most participants reported short-term sexual behavior changes after a syphilis diagnosis to prevent transmission; however, few were willing to make long-term behavior changes. CONCLUSIONS: Additional qualitative studies of men who have sex with men should be conducted to better understand the continuing syphilis epidemic and to help identify the most promising intervention strategies.