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Jenna was born in Las Vegas, Nevada. Her mother died of skin cancer on February 20, , when Jenna was two years old, after which she became very close to her brother, Tony Massoli. In , at age 16, Jenna was thrown out of her home and moved in with her boyfriend, a tattoo artist, with whom she had her first serious relationship. She applied for jobs as a dancer in Las Vegas, and in , she began dancing in strip clubs with the help of a fake I. Initially rejected from dancing at the Crazy Horse Too strip club because of her braces, they quickly relented when she removed them with the aid of her brother and a pair of needle-nosed pliers.