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In May 2001, Village Voice columnist Michael Musto said that Sullivan had anonymously posted advertisements for bareback sex (anal sex without a condom) on America Online and the now-defunct website barebackcity.com, despite being HIV positive.^[71] An archive copy of the advertisement is still available.^[72] Subsequently, the American journalist and activist Michelangelo Signorile wrote about the advertisement in a front-page article in the New York gay magazine LGNY, igniting a storm of controversy.^[73] Later, in a defiant blog post titled Sexual McCarthyism: An article no-one should have to write, Sullivan confirmed the allegations, admitting he had posted the adverts, while nonetheless arguing that the matters covered by the controversy were private and should not have been put into the public domain by his critics.^{[74][dead link]}

Sullivan's critics^[73] argued that it was hypocritical of Sullivan to engage in this kind of sexual activity while arguing for greater monogamy among gay men. They claimed that the vision of gay sexuality presented in Sullivan's writing was at odds with his alleged activities. They charged that because Sullivan is HIV-positive, it was unsafe for him to engage in sex without a condom. Sullivan's critics^[75] contended that it was unfair for Sullivan to criticize Bill Clinton's sexual indiscretions as "reckless" while engaging in unprotected sex.

Sullivan responded that his advertisement stated that he was HIV-positive and he intended to have bareback sex only with consenting adults who were HIV-positive. According to Sullivan, limiting unprotected sex to other HIV-positive men reduces the risk inherent in the behavior. Moreover, he criticized what he called a "thin reed of evidence" of the existence of "reinfection" which, according to some medical professionals, heightens the destruction caused by the virus.^[76] Sullivan's supporters argued that it was a violation of his privacy to publish information about his sex life.^[77] Sullivan argued that those who revealed the details about his sex life were motivated by a desire for payback because they disagreed with his pro-marriage politics .^[74] In Sullivan's book Love Undetectable (pub. 1999), he wrote:

"Although I never publicly defended promiscuity, I never publicly attacked it. I attempted to avoid the subject, in part because I felt, and often still feel, unable to live up to the ideals I really hold."^[78]