Usher Wishes He Could Have Dated Aaliyah

Usher has been associated with a number of well-known women and has almost no regrets in his life. But he does have one individual he wishes he would have held to a higher standard and dated back in the day, according to a recent interview.

On Tuesday (March 1), during an interview on EDaily !’s Pop, the R&B star broke the news that has fans pondering what could’ve been. Usher was asked to take part in a game called “Confessions,” in which he was asked about a celebrity he wishes he could have dated back in the day. That’s when the “Yeah!” singer talked about how he regrets never starting a relationship with fellow music legend Aaliyah when he had the chance, especially since they were such good friends.

“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. 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 his first celebrity kiss was with, and he said Monica, an R&B singer. She’s a good kisser, according to Usher. Monica made an appearance on Usher’s 1997 album My Way’s song “Slow Jam,” which will be remembered by longtime Usher fans. Prior to it, the two were said to have dated for eight months in 1995.

Usher is no more out on the streets, as he and his wife welcomed a baby boy into the world in September 2021. The singer said during a recent interview on Ellen Degeneres’ talk program that 50 Cent’s “In Da Club” was playing when his baby son was being born. However, 50 was overjoyed by the news and congratulated Usher on Instagram.

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