Usher Wishes He and Aaliyah Dated
Usher was once of the most vied after sex symbols in music. But several women have captured the singer’s attention. Usher has been married and divorced a few times, and his most beloved relationship with TLC singer Chilli. But there’s one person Usher wishes he’s had a romantic relationship with: Aaliyah. The two were close friends but never took it beyond that.
Usher has regrets about not dating Aaliyah
In the 90s, Usher and Aaliyah co-hosted several events together and appeared in magazines together. It made since with both of them being two of the hottest stars of the time. Looking back, Usher wishes his relationship with Aaliyah was more than platonic.
“Somebody that I was really good friends with that I wish I would have taken more serious,” he said in a recent interview, per The Jasmine Brand during Usher’s recent appearance on E! News’ Daily Pop. “Beause she was a really, really close friend of mine for a small amount of time…And then we just kind of disconnected–it was Aaliyah.”
He continued: “And we just didn’t get around to it, we just kinda talked but didn’t do it.” At the time, Usher was linked to a lot of teen heartthrobs, including Monica and Brandy, the latter of which he starred alongside as Brandy’s character on Moesha’s love interest as Jeremy. He’s denied dating them all.
On whether or not he and Aaliyah ever considered dating, Usher added: “No, we were friends, we hung out. We watched movies together and hung out. But it didn’t go there.”
He’s been married twice
The 8701 singer did eventually find love elsewhere. He married celebrity stylist, Tameka Foster. Their relationship was controversial from the beginning.
Before they even walked down the aisle, there were signs of trouble. A day before their scheduled nuptials, Usher called off the wedding. Foster was five months pregnant with the couple’s first child at the time. He later told Oprah Winfrey that he wasn’t ready to walk down the aisle. In a twist, they married months later in an intimate civil ceremony. Usher’s mother did not attend and was against their wedding from the start.
Usher and Foster had two sons together: Usher V and Naviyd. In 2007, Usher filed for divorce after just two years of marriage, citing irreconcilable differences. Foster accused him of cheating. Usher told Oprah that help did sleep with one of Foster’s bridesmaids after they split. He also said he had “emotional affairs.”
He married Grace Miguel, his manager, in 2015. They split in 2018 amid news of Usher having herpes becoming public. It was also rumored that Miguel wanted children and Usher did not.
Usher is now dating music executive, Jenn Goicoechea. They have two children together.
Many remember him for his relationship with Chilli of TLC
Usher and Chilli dated from 2001 to 2003. During their relationship, Chilli made appearances in Usher’s music videos, including “U Got It Bad.” In a VH1 interview special, Chilli told producers that their split was not because of Usher’s alleged infidelity, which he sung about in his song “Confessions” and the album title of the same name.
“I never thought of him cheating,” she said. “I don’t know…I didn’t expect anything like that from him because of how much we loved each other,” Huffington Post reports.
But, Chilli did admit that she was hurt by Usher beginning another relationship quickly after their split. “I kept hearing about it, then I went to him and I asked him and he admitted it. You know I just, I felt like a fool, I felt like everybody knew something and I didn’t, and I’m just now finding out,” she added.
More than anything, Chilli was irritated over the belief that Usher’s album was a public diary into their relationship “So people assumed that album was about us, but it was not,” she said. “And Usher and I weren’t oil and water. We broke up because, I guess, it was that time or whatever. He was that real love for me.”
