Schlessinger was born in the New York City borough of Brooklyn. She was raised in Brooklyn and later on Long Island. Her parents were Monroe "Monty" Schlessinger, a civil engineer, and Yolanda (nee Ceccovini) Schlessinger, an Italian Catholic war bride. Schlessinger has said her father was charming and her mother beautiful as a young woman.

On August 10, 2010, Nita Hanson, a black woman married to a white man, called Schlessinger's show to ask for advice on how to deal with a husband who did not care when she was the subject of racist comments by acquaintances. Schlessinger first replied that "some people are hypersensitive" and asked for some examples from the caller. Hanson informed Schlessinger that her acquaintances had stated, "How you black people do this? You black people like doing that." Schlessinger responded that her examples were not racist and that "a lot of blacks only voted for Obama simply because he was half black. Didn't matter what he was going to do in office; it was a black thing. You gotta' know that. That's not a surprise." Schlessinger continued by telling the caller that she had a "chip on [her] shoulder," was "sensitive," and also, "Don't NAACP me," and, "a lot of what I hear from black think... it's really distressing and disturbing."  When the caller noted that she was referred to as the "n-word" by the individuals in question, Schlessinger complained that blacks are fine with cordially using the slur among themselves, but that it was wrong when whites used it to slur them. In doing so, she uttered "nigger" eleven times, albeit not directed at the caller. She discussed the word and its use by blacks and in black media. Her profuse use of the slur was mimicking the frequency of the word's use among black stand-up comics. When Hanson asked, "Is it ever OK to say that word?" Schlessinger responded, "It depends how it's said. Black guys talking to each other seem to think it's OK." After the call Schlessinger said, "If you're that hypersensitive about color and don't have a sense of humor, don't marry out of your race." Early that evening she wrote an apology to Los Angeles Radio People online journalist Don Barrett. A day later, as soon as she was back on the air, Schlessinger apologized. Hanson questioned the motivation and sincerity of Schlessinger's apology, believing it to be result of being "caught." Hanson also said that Schlessinger did not apologize for her comments on interracial marriage.  Schlessinger announced that, while not retiring from radio, she would end her radio show at the end of 2010:  I have made the decision not to do radio anymore. I want to regain my First Amendment rights. I want to be able to say what is on my mind.  In 2011, she began broadcasting on satellite radio with Sirius XM. Her program is also available as a podcast at iTunes and from her own website.

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