The 43-year-old singer revealed that he was “really close friends” with the pop star — who died in an airplane crash at the age of 22 back in 2001 — and regrets not taking things more seriously with her.
Asked which celebrity he would have dated if he had 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 seriously because she was a really, really good friend of mine for a small amount of time and then we just disconnected was Aaliyah. I think I would have dated Aaliyah.”
The “Yeah!” hitmaker — who is currently dating Jenn Goicoechea and welcomed son Sire Castrello Raymond with her back in October 2021 —went on to explain that he would often “hang out” with the “More Than a Woman” singer before her death.
He told E! News’ Daily Pop: “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.”
Usher — who also has daughter Sovereign Bo, 18 months, with Goicoechea, as well sons Naviyd Ely, 12, and Usher V, 13, with ex-wife Tameka Foster — also revealed that his first celebrity kiss was with “Like This and Like That” hitmaker Monica.
He said: “My first celebrity kiss [was with] Monica. Monica Arnold. She was a good kisser!”