When asked which celeb he would have loved to date if he had gotten the chance, he said: “I’ve never told anyone this before. Somebody that I was really good friends with that I wish I would have taken more serious because she was a good friend of mine for a small amount of time, and then we just disconnected was Aaliyah. So I think I would have dated Aaliyah.”
The hitmaker is currently seeing Jenn Goicoechea and welcomed a son, Sire Castrello Raymond, back in October 2021. Usher went on to make it clear that he would mostly “hang out” with the ‘More Than a Woman’ singer before her tragic demise.
Speaking with E! News Daily Pop, he said: “We just didn’t get around to [dating] . We just kind of talked but didn’t end up doing it. We were friends and hung out. We watched movies together, but it just didn’t go there.”
The award-winning singer also disclosed that his first celebrity kiss was with ‘Like This and Like That’ hitmaker Monica.