The R&B heartthrob dropped a bombshell that has fans wondering what could’ve been. The show’s host had Usher participate in an aptly-titled game called “Confessions,” where he was asked about a celebrity that he wishes he could’ve dated back in the day. That’s when the “Yeah!” singer revealed he had a chance with the late Aaliyah “Somebody that I was really good friends with that I wish I would have taken more serious because she was a really close friend of mine for a small amount of time and we just kind of disconnected was Aaliyah,” he said. “I think I would’ve dated Aaliyah and we just didn’t get around to it. We just kind of talked but didn’t do it. Usher was then asked who he shared his first celebrity kiss with, to which he replied R&B songstress Monica According to Usher, she’s a pretty good kisser. Longtime Usher fans will remember Monica appeared on his 1997 album My Way on the song “Slow Jam.” Before that, the pair reportedly dated for eight months in 1995.
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