The R&B superstar revealed that he missed out on a romantic relationship with Aaliyah. Speaking with E! News’ “Daily Pop,” Usher was asked which celebrity he would have dated back in the day if he had the chance.
“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 regrets the missed love connection. “I think I would have dated Aaliyah and we just didn’t get around to it.”
While he wishes he made a move, the two kept their relationship in the friend zone. “We just kinda talked but didn’t do it,” he added. “We were friends, we hung out, we watched movies together and hung out but it didn’t go there.”
Usher is currently in a relationship with the mother of his two kids, Jenn Goicoechea. The couple welcomed their second child, a baby boy, in October. The singer also has two sons, Usher and Naviyd, with ex-wife Tameka Foster.
Aaliyah famously dated Damon Dash and was briefly married to R. Kelly.
In July, Usher will return to Las Vegas for his new residency at Dolby Live at Park MGM, which he promises will be “more theatrical.”