In 1995, he founded Q Syndicate, a gay-press syndication service that provides columns, cartoons, crossword puzzles and horoscopes to about 100 gay and lesbian newspapers. In 1999 he founded Press Pass Q, a monthly e-mail newsletter for gay and lesbian press professionals. In 2001, he sold a majority interest in Q Syndicate to Rivendell Marketing, and served as vice president for two years before selling the rest of the company. In 1997 Benkof wrote Modern Jewish History for Everyone and in 1999 Gay Essentials: Facts for Your Queer Brain. In 2002 and 2003 he wrote the column “Over the Rainbow” for Q Syndicate.
In 2003, he announced that for religious reasons he had stopped having sex with men. He has always been a devout Jew, and says that one reason he changed was because "Gay sex is just inconsistent with traditional religious life." To reflect his change in sexual identity, and to honor his late grandfather, Julius Benkof, David Bianco changed his name to David Benkof. He still identifies as a gay man, and has criticized the Ex-gay movement, and expressed his opinion that "reparative therapy doesn’t work".
He has since become a strong opponent of same-sex marriage. In response to arguments for gay marriages, he wrote "This reasoning is not only flawed, it insults the millions of Americans whose traditional faiths call on us to defend marriage as a central institution in society defined as a union between a man and a woman." Benkof has made it clear that his objection to same-sex relationships is based in part on his personal religious beliefs, stating, "I happen to believe that God has been clear to the Jewish people that we should be pursuing opposite-sex relationships, and particularly not having intercourse between two males."
For two months in 2008 he was actively involved in the campaign for California Proposition 8 (2008), and to support this campaign he started a blog called Gays Defend Marriage. But in July 2008 he broke with the campaign and closed the blog, writing that while he continued to oppose same-sex marriage he had lost respect for its organizers, and accusing them of tolerating antisemitism and homophobia.
In 2014, Benkof wrote an op-ed piece in the Times Of Israel called Orthodox, celibate, gay and that’s OK in which he dismissed arguments in favor of reinterpreting the Biblical prohibition on homosexuality. He stated his "message for Orthodox gays": For men like us, following Jewish law about sexuality is an enormous struggle which often takes place without much sympathy or support. God loves us even when we cannot understand why He would limit our sexual options. Ideally, we’ll never have any sort of intimate contact with other men. But any exceptions should be as infrequent as possible, with as few halachic violations as possible. Be especially careful to avoid mishkav zachar. The process of teshuvah exists precisely so people in such situations can pick themselves up, rectify their behavior, and move on. Take advantage of it.
In June 2016, Benkof made it known that he no longer believes in Orthodox theology (though he continues to belong to an Orthodox synagogue), and that he no longer wishes to be described as celibate, "or any other bedroom status".
Benkof spent the 2004-2005 year at Darche Noam/Shapell's, an Orthodox yeshiva in Jerusalem. He then studied at the Hebrew University in Jerusalem during the 2005-2006 academic year. From 2006-2008 David pursued graduate work in American Jewish history at New York University. In 2008 and 2009 he wrote a weekly column, Fabulously Observant, for the Jerusalem Post and several other Jewish newspapers, discussing "life from the perspective of an Orthodox, conservative, openly gay American Jew in the process of making aliyah". He returned to Darche Noam/Shapell's from 2011 to 2014 as a teacher of Hebrew grammar.