R&B legend Usher, 43, opened up about his friendship with the late Aaliyah and confessed that he regrets not dating her. When asked which celebrity he would’ve dated in the past if he had the opportunity, he answered: “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 continued: “And we just didn’t get around to it, we just kinda talked but didn’t do it.” Audio *Here*