R. Kelly’s Ex-Girlfriends & Dating History: 5 Fast Facts

Getty Pictured: R. Kelly

R. Kelly’s personal life is the subject of the Lifetime miniseries Surviving R. Kelly 2. He has been linked to several different women throughout his career, some of whom were underage and many of whom have accused the singer of emotional and sexual abuse.

Kelly has also dated other R&B singers and celebrities like Aaliyah and K. Michelle. Read on to learn more about Kelly’s romantic history, as well as his list of ex-girlfriends. Here’s what you need to know:

1. Kelly Dated R&B Singer Aaliyah When She was 15

Kelly’s first public relationship was with musical protege Aaliyah. He met the future star when she was only 12 years old, and by the time she was 15, they had struck up a romance. Kelly wrote and produced Aaliyah’s debut album Age Ain’t Nothing But a Number, and by August 1994, the couple was married. According to the New York Times, Kelly bribed an Illinois governor in order to obtain a fake ID for his bride. The fake ID said that Aaliyah was 18 at the time.

Kelly and Aaliyah tried to keep their marriage a secret, but the latter’s family eventually found out and were outraged. According to the Chicago Sun-Times, they demanded the couple get an annulment right away, which they did in 1995. Their professional relationship came to an end soon after. Aaliyah continued to release music as a solo artist until her untimely death on August 25, 2001. She was 23.

Kelly has refused to discuss his relationship with Aaliyah out of respect for her memory. Damon Dash, who was dating Aaliyah at the time of her death, appears in Surviving R. Kelly 2, and he says that the singer was relieved to get away from Kelly. “Aaliyah was like the sacrificial lamb for all that, she didn’t deserve none of that,” he revealed. “Good soul, good girl, weren’t so resentful, like let that man live, but just keep him the f*ck away from me. That’s all she wanted.”

2. Singer K. Michelle Said She Felt ‘Trapped’ When She Dated Kelly

R. Kelly and K. Michelle had a mentor-protege relationship similar to that of Aaliyah. During a 2018 episode of Uncensored, Michelle said that Kelly helped her land a record deal and served as a musical influence, but that things turned sour when they struck up a romance. She claimed that Kelly forced her to stay in his house and cut off all contact with her family.

“Being in that house offered its own set of dysfunctional issues for me,” Michelle revealed. “I remember feeling trapped. If I leave this house, I’m never going to sing. I’m having to stay there. I don’t see my family. I don’t see anybody but R. Kelly.” After she broke things off, Michelle said that Kelly refused to speak to her. “He really wouldn’t talk to me. I lost my friend and my mentor,” she remarked. “A lot of my career and a lot of the things that I went through [at] the core of it was a man.”

K. Michelle has continued to speak out against Kelly. She released the song “Build a Man” on her 2014 album Anybody Want a Heart, which is a direct diss at the singer. She said she wants to make sure that Kelly doesn’t manipulate any more women. “I do feel like it’s my obligation as a woman to tell the truth and to do right by other females that are in the business and all these young women who don’t have a voice,” she told Billboard.

3. Kelly Dated Author & Singer Jara Everett When She Was 19

Kelly had a brief tryst with author and entertainer Jara Everett when she was 19. The latter detailed their relationship in the book The Jump Off: The Real Truth, where she said that Kelly introduced her to various sexual acts, and the “craziness” of the celebrity lifestyle as a whole. “He was different, he sort of introduced me to some craziness, [like] the golden shower thing,” she told YouTuber Toxsique Diamond. “There was nothing ‘lover’ about it, it was what it was it was a long time ago.”

Despite her insistence that her time with Kelly was not serious, Everett said the singer gave her a useful piece of advice. “When I dated Suge [Knight], I learned how to be a boss. When I had a thing with R. Kelly, I was younger, this was before I dated Suge,” she recalled. “[Robert] taught me one thing, he said, ‘Hey, if you want this music business you might have to have sex with people you might not want to if you want to get to the top.’ That’s the way it is.”

Everett has several entertainment credits to her name. In addition to being an author, she used to sing with the R&B group S.T.O.P. and was crowned Chicago’s Most Beautiful Girl at the 1995 Miss Illinois Pageant.

4. Kelly Dated Maxine Daniels, the Daughter of His Publicist

Kelly had a relationship with Maxine Daniels, the step-daughter of his longtime publicist Regina Daniels. The latter quit her position as publicist upon discovering the relationship, and said that the singer had “crossed a line.” Regina’s husband George also spoke out against Kelly, saying that he knew their daughter since she was 7, and that she was like “his sister.”

George felt that Kelly had preyed upon his daughter, who was 21 at the time the relationship took place. “When a child is sidetracked, when a child is persuaded to lie, to go against [her parents’ wishes], when you have the toys and the gifts and the shopping sprees … that’ll turn anybody,” he told MTV. Kelly’s representatives said that the Daniels family knew about the relationship, but they denied these claims outright.

Maxine Daniels broke her silence in 2008. “I take full responsibility for my actions,” she told the Chicago Sun-Times. “My stepmother and father didn’t know about my relationship with the singer because I knew and he knew that they wouldn’t approve … so I tried to keep it a secret, but when my stepmother found out about our relationship, she resigned because she felt that Rob had ‘crossed the line’ by dating a girl that he has known since she was seven years old.“

5.  Kelly Was Last Seen Dating Aspiring Singer Azriel Clary

Kelly first met Azriel Clary when she was 16. He took up an interest in her singing talents, and they began working together, but Clary decided to cut off contact with her family when she turned 18. Clary’s parents appeared in the miniseries Surviving R. Kelly, where they said they hadn’t seen their daughter in over four years.

It’s unclear whether Kelly and Clary are still dating, but TMZ reports that Clary has decided to distance herself from Kelly’s legal troubles and move out of his Trump Tower condo. She now has her own place in Chicago, and has revived her singing career. She’s also reconnected with her family, as she had a Twitter exchange with her father on December 29, 2019.

Clary has not spoken out against Kelly, but she did issue a statement on Twitter that detailed her stance on privacy. “If you think I created social media to publicize my private life your sadly mistaken,” she wrote. “If I choose to share, say or not say anything that is 100% my choice whether now or in the future. Love me or hate me I’m not here to appease you, nor am I your gossip outlet.”

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