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Usher Regrets Not Dating Aaliyah and Confesses Singer Monica Is a ’Good Kisser’

Usher Raymond disclosed in a recent interview with E! News’ “Daily Pop” the one celebrity he regrets not dating.

The singer, who was promoting his second Las Vegas residency set to begin this summer, told the news outlet on March 1, that he wished he had taken the next step with Aaliyah Haughton.

Usher reveals during an interview with E News! “Daily Pop” that he regrets not dating Aaliyah. Photo:@e!news/YouTube

The 43-year-old said, “I never told anybody this but I’ll give you an exclusive: Somebody that I was really good friends with that I wish I would have taken more serious ’cause 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 added, “I think I would have dated Aaliyah. We just didn’t get around to it. We just kind of talked but didn’t do it.” When asked if busy schedules were the reason behind the pair’s decision not to date, Raymond quickly responded, “No, no, no; we were friends. We hung out, you know what I’m saying. We’ll watch movies together and hang out, but it didn’t go there.”

Raymond went on to be in several high-profile relationships, including with Rozonda “Chilli” Thomas, Tameka Foster and Grace Harry. The “Confessions” singer is currently dating music executive Jenn Goicoechea. Prior to Haughton’s passing in 2001, following a plane crash in the Bahamas, she was dating record executive and entrepreneur Damon Dash.

As Raymond’s response began circulating on social media blog sites, many fans reacted by expressing that the father of four wasn’t the only one that wanted to be with Haughton.

“Everybody wanted Aaliyah; she really was a dream.”

“We all would’ve dated Aaliyah.”

“Who didn’t want to date Aaliyah though??? Lmao.”


Among the previous remarks, others claimed if Raymond and Haughton did date, they would have made a cute couple. One wrote, “I would have been here for it!!! Usher and Aaliyah would have been the cutest couple!!!” Another said, “I think him and Aaliyah would’ve been so cute.”

Also, in the interview, Raymond shared that his first celebrity kiss was with his “Slow Jamz” collaborator Monica Arnold. He went on to describe Arnold as a “good kisser.”

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