Usher Regrets He ‘Didn’t Get Around’ To Dating Aaliyah Before Her Death

Usher has some regrets about his romantic life!

During an appearance on E! News’ Daily Pop on Tuesday, the 43-year-old singer played a game of Confessions where he was asked about who he would have dated back in the day. And what he says may or may not shock you!

Of course Usher is now involved with Jenn Goicoechea, and the couple shares two children together, Sire and Sovereign. But when he casts his mind back, he can still think of one that got away: Aaliyah!

Related: Dax Shepard Reveals He Dated Ashley Olsen!

Usher admits he regrets never shooting his shot with the Queen of the Damned star when he had the chance. The My Boo artist admits:

“Somebody that I was really good friends with that I wish I would have taken more serious. 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. I think I would have dated Aaliyah.”

Woah! So why did their romance never happen? According to Usher, the pair sadly “didn’t get around” to dating despite hanging out as friends.

And of course, the iconic R&B performer tragically passed away in a 2001 plane crash. It’s a real warning to people not to take things for granted. The people you think will be around later may be gone before you know it…

In the vid, Usher also talks about some romances he didn’t miss. For instance, his first celebrity kiss was with Monica — who he excitedly exclaims was a “good” kisser.

Ch-ch-check out the entire game with Usher (below):

Are you surprised Usher regrets not dating Aaliyah? Let us know your reactions to his confession in the comments (below)!

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