(Older man walks by.)
LORELAI: Because I’m not Anna Nicole Smith. Next.
(Teenage boy on a skateboard goes by.)
LORELAI: Hmm, pass.
LORELAI: Because I’m not Mary Kay Letourneau.
Anna Nicole Smith, born Vickie Lynne Hogan (1967-2007) [pictured] was an American model and actress who first gained fame as a Playboy model, winning Playmate of the Year in 1992. She was perhaps best known for her 1994 marriage to J. Howard Marshall, an 89-year-old petroleum tycoon she had met while working at a strip club. It was speculated that she had married him for his money because of the age difference. Marshall died the following year, and there was a protracted legal case over his will; during it, Smith herself died, gaining no money from his estate.
Mary Kay Letourneau (born Mary Katherine Schmitz in 1962) is an American former schoolteacher who in 1997 pleaded guilty to raping a child, her twelve-year-old student Vili Fualaau, to whose baby she gave birth while awaiting sentencing. Due to a plea agreement, she was sentenced to three months in prison, and was not allowed contact with Fualaau for life. She broke the no-contact order soon after being released from prison, and was imprisoned again, this time for seven years, giving birth to another child in prison. After Letourneau was released in 2004, Vili Fualaau, now an adult, asked that the no-contact order be revoked, and they married in 2005. They legally separated in 2017, although they apparently still live together and are still in a relationship.