Pop legend Michael, 50, has met the 41-year-old former 'Baywatch' star for two dates in Malibu, California.
A source told Britain's Daily Mirror newspaper: "It was all arranged by their people in total secrecy, very cloak and dagger. Michael is such a private person. He gets nervous when he thinks people are following him around, so he chose somewhere neutral for their first date.
"They arrived separately at the Shutters Hotel on Malibu beach so no one would suspect anything and then had a few drinks at the bar."
Jackson and Anderson hid away in a corner of the bar for privacy, and appeared to be enjoying each other's company.
The source added: "They were very friendly. Pamela was being her usual flirty self and Michael seemed to be responding. They are such a strange couple but they seemed to really hit it off."
The pair got on so well on their first date, they have met up again already, going for a coffee at the Country Mart in Malibu.
Both Anderson and Jac kson have been unlucky with their previous marriages.
Jackson has been married twice, to Lisa-Marie Presley and nurse Deborah Jean Rowe.
Anderson has tied the knot three times, to Motley Crue rocker Tommy Lee, Paris Hilton's ex Rick Salomon and Kid Rock. None of Michael or Pammie's marriages lasted more than three years.
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