During an interview Raymond was asked who he would have dated back in the day, with no hesitation Usher said he would have dated Aaliyah. The two were good friends and for a short period of time they hung out consistently.
Raymond opened up to the details with E. News as he has been doing many interviews to promote his Las Vegas residency.
The Grammy Award-winning artist, 43, will take the stage at Dolby Live at Park MGM for 23 dates from July-October after selling out every date at his 20-show residency at The Colosseum at Caesars Palace in 2021.
During a recent interview with “Good Morning America,” the singer spoke about what changes he’s making with his new shows and how he selects which songs from years of massive hits to perform during the residency.
“The idea that Las Vegas is still Sin City is what’s in my mind,” he said. “It’s now become a place that is commercial enough for everybody to come and have a good time. Yeah, you can bring your kids and you can have a good time, but it’s still Sin City to me.”
However, it was the interview with E News that everyone is talking about, when Usher says that he would have dated Aaliyah. “I’ve never told anybody this,” he admitted. “Somebody that I was really good friends with that I wish that 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 kinda disconnected—it was Aaliyah.”
Usher hash paid tribute to his late friend on several occasions since her still-shocking death on August 25, 2001 in a plane crash. From singing “It’s So Hard to Say Goodbye to Yesterday” in her memory on both 106 & Park and Live with Regis and Kelly, he would also wear an Aaliyah tribute T-shirt at the 2001 VMAs that occurred exactly two weeks after the accident in addition to in the music video for his 8701 single “U-Turn.”
He also admitted that his first real kiss was with Monica Brown.
Knowing how Aaliyah could quickly place someone in the friend zone do you think Usher had a chance?
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