Usher is opening up about his celebrity missed connections.

In an interview with E! News’ “Daily Pop” talk show, the artist was quizzed on his celebrity relationships and which crush he wished he had acted on.

“Somebody that I was really good friends with that I wish I would have taken more serious, ’cause 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,” he admitted of the late singer.

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The two were close with Usher dedicating tributes to her over the years and speaking of her fondly. She died in a plane crash in 2001 at the age of 22 and was dating Roc-A-Fella co-founder Damon Dash at the time.

When asked why their relationship never turned romantic, Usher said it was just a matter of timing.

“And we just didn’t get around to it, we just kinda talked but didn’t do it,” he added.

The 43-year-old also dished on his first celebrity kiss, which was with the singer Monica.

“Yeah, she was a good kisser,” he confirmed.

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Usher is currently dating Jennifer Goicoechea, director of the rhythm and soul department at ASCAP. They welcomed their second child Sire in late September.

While he may be one of the titans of the music industry, his kids don’t think much of it.

“I don’t think there’s anything I can do to make them understand how cool I am,” he said when asked whether his kids think he’s cool. “And I try. Don’t get me wrong. I don’t let them win in games to win favouritism so they’re probably against me.”

The R&B artist is father to 12-year-old Naviyd Ely and 13-year-old Usher V with his ex-wife Tameka Foster, along with baby Sovereign Bo and Sire with Goicoechea.

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While he may not be the coolest dad in the world to his kids, he’s happy to have that work-life separation.

“I get that fortunate ability to create balance between being this dad that I never had and also to being able to report to my day job which is this artistry,” said Usher.