George Michael and Brooke Shields briefly dated in 1985. Shields, then 19, was still a virgin and Michael respected that, keeping the relationship chaste. Shields’ mother was a fan of Wham! and contacted Michael’s publicist, saying her daughter wanted to meet with him. Michael agreed to meet with Shields and arranged a dinner meeting. Their first date took place on top of a rooftop of a Chicago hotel. The relationship ended at a star-studded party for Grace Jones. Shields was devastated and cried herself to sleep for weeks.
Shields went on to have a highly-publicized romance with another Michael, MIchael Jackson, and is now married to writer Chris Henchy with two daughters. Michael came out as gay in 1998, although he identified as bisexual during his relationship with Shields. Michael’s conflict with his sexuality led to depression and guilt over having female relationships, which is why he broke up with Shields so abruptly.
“I had a crush on George Michael. Mom had decorated a denim shirt of mine with ‘WHAM’ in glitter paint and Bedazzles. She glued pins and little pictures of George and surprised me with it to wear to his concert.”
“We got into the limo and headed back to my home in New Jersey. As we were nearing the house, George put up the partition and turned to me. I thought, Oh God–I’m going to have my first time with George Michael in the back of the limo! Forget Catholicism and the book. Forget my mother. God would understand! I gazed at George with puckered lips. He looked deep in my eyes and said, ‘I think we need to take a break. I need to concentrate on my career.’ WHAM!”