British pop superstar George Michael died Christmas Day from heart failure, leaving fans around the world in shock. The “Last Christmas” singer was 53 years old.

During his career spanning over 30 years, Michael was known for run-ins with law and high-profile relationships, including a brief one with American actress Brooke Shields. However, Michael was never married and was not involved with any one at the time of his death.

Michael was most recently spotted with Fadi Fawaz in Switzerland in September 2015. Fawaz, who is reported to be a celebrity hairdresser, was rumored to be Michael’s boyfriend. The two were photographed holding hands at the time. However, Michael maintained secrecy about the rumored relationship and never publicly commented on it.

Prior to Fawaz, the British pop superstar was involved in a long-term relationship with Kenny Goss, a Texas-born businessman. The two began dating in 1996 and were together for 13 years. In 2011, Michael announced onstage that he and Goss parted ways. Prior to their breakup in 2009, reports surfaced that the two were contemplating getting married. On Monday, the Sun reported the former lovers had been in contact again in recent months.

After he rose to fame in the 1980s, Michael admitted he struggled with his sexuality and called the time during his late 20s a depressing period. He came out as gay in a 1998 CNN interview, saying: “This is as good of a time as any. I want to say that I have no problem with people knowing that I’m in a relationship with a man right now. I have not been in a relationship with a woman for almost 10 years.”

In the 1990s, Michael was in a relationship with Anselmo Feleppa, a Brazilian dress designer, whom he met at the 1991 concert “Rock in Rio.” He lost Feleppa to AIDS at a time when the gay community was struggling with the disease. Michael dedicated his single “Jesus To A Child” to his deceased lover. The British singer also confessed it took him several years to recover from Feleppa’s death.

It was after Feleppa’s death that Michael wrote a letter to his parents confessing he was gay. In a 2004 interview with GQ magazine, Michael said his mother was devastated because she had not been able to help him through the traumatic experience of his coming out. He also said it was hard for his father to deal with the fact, but he never “displayed any disappointment or homophobia.”

“I’m sure he felt it, and it was hard for him, but he didn’t lay any of it onto me which I have to thank him for. This is sad, but I do feel success can negate a parent's disappointment. I genuinely feel that although his son is gay and not going to give him any grandkids, my dad's consolation is that I have done well in life,” Michael told the magazine at the time.

In 1985, he briefly dated Brooke Shields and the two went on their first date on the rooftop of a hotel in Chicago. In the same GQ interview, Michael spoke about his relationships during his days in Wham!

“I used to sleep with women quite a lot in the Wham! days but never felt it could develop into a relationship because I knew that, emotionally, I was a gay man. I didn't want to commit to them but I was attracted to them. Then I became ashamed that I might be using them. I decided I had to stop, which I did when I began to worry about AIDS, which was becoming prevalent in Britain. Although I had always had safe sex, I didn’t want to sleep with a woman without telling her I was bisexual. I felt that would be irresponsible. Basically, I didn’t want to have that uncomfortable conversation that might ruin the moment, so I stopped sleeping with them,” Michael said at the time.