From Frank Cascio’s book “My Friend Michael.” Based on the time that Frank spent working and was most around MJ, either 2000-2001 or 2001-2002 seems to be the most likely time period for this relationship. Frank began working for MJ in June 1999, and MJ was married to Debbie until October 1999, and he says that this relationship occurred around a time Michael visited London with him, which was in March 2001.
From “My Friend Michael,” by Frank Cascio
Sometimes Michael invited members of his fan clubs to Neverland, and he occasionally formed a special relationship with one of the women. One time I was driving Michael into town. Someone was next to me in the passenger seat of the Bentley, and Michael was in the backseat, kissing one of his fans.
“Easy back there,” I said. “Relax, calm down.”
“Just keep driving,” Michael said in a joking way. “Don’t worry about it, just keep driving.”
Michael’s dalliances with fans were infrequent and discreet, but they were hardly unheard of. He tended to like tall, slender women whom I’d describe as nerdy in a sexy way. Once, in London [March 2001?], I was in his suite when he brought a friend he’d known for years into his bedroom. They were in there for about an hour, and when he emerged, his pants were unbuttoned. I smirked at him.
“Shut up, Frank,” he said, smiling sheepishly. The woman, equally sheepish, said goodbye and left.
Around this time, Michael had another friend – I’ll call her Emily – who visited the ranch regularly. She was a nice, cute girl, slender, with brown hair, in her early to midthirties. Emily didn’t want or need anything from Michael. They just liked spending time together – talking, walking around, hanging out in his bedroom. It was a romantic relationship, but as far as I know, he didn’t tell anyone about Emily but me. Michael kept her a secret – she didn’t stay in his room because he didn’t want her to be seen coming out in the morning – and even I didn’t see real evidence of the romance. That’s how I knew he was telling the truth. He wouldn’t have been so secretive if he hadn’t had something to hide. That was the longest relationship I saw Michael have: Emily was at the ranch frequently over the course of about a year.
The question as to whether Michael was intimate with Debbie Rowe came up often. People seemed to think that they could make sense of Michael if they could only unravel the mystery of his relationships with women, but Michael was his own man. There were no simple answers. I know he was sexually intimate with Lisa Marie when they were together – he told me so. With Emily, to be honest, I’m not sure, but I know in her he found a companion, a friend.
Frank shows a personal side of Michael, sharing stories about him kissing and dating numerous women. He agreed that Michael’s attraction to women was something that generally wasn’t focused on.
“It was downplayed. And I’ll tell you, Michael was private about that part of his life. Michael was attracted to women. He had a very particular type and it’s funny because people wouldn’t think it, but it’s a simpleton. He was dating this girl who he really cared about and you know and she cared about him and it was great to see, but it was also kept very private because Michael did not want to, you know, expose this girl and have the media from the outside ruin a relationship that he really was enjoying and you know, he likes slender, tall, simpletons, sweet, humble, soft-spoken girls. And I’m really happy that Michael actually found that in his life later on.”