Usher has had several high-profile romances over the years, but on Tuesday (March 1) he revealed the one that got away. The father of four sat down with E! Online’s “Daily Pop” and admitted he regrets not pursuing a relationship with Aaliyah.

“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,” Usher revealed to the outlet. “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 explained that he and the late star were “good friends,” but never took their relationship to the next level.

“We were friends, we hung out. We’d watch movies together and hang out, but it didn’t go there,” he said.

Usher also revealed that Monica was his first celebrity kiss, adding that the “So Gone” songstress was “a good kisser.”

As reported by REVOLT, the 43-year-old will return to Las Vegas this summer for a 23-show residency. The slated shows kick off on July 15 at Dolby Live at Park MGM and run through Oct. 29.

“In Las Vegas, you get an opportunity to be more theatrical,” he said during his E! interview. “… For me, the effort was to try to be theatrical, but mindful of my culture and where I come from.”

Usher welcomed his fourth child, and second with his girlfriend Jenn Goicoechea, last October. He recently shared a video of the newborn’s first moments, during which 50 Cent’s “In Da Club” was playing.

“Me and 50, we talked about it. It felt cool to introduce him to the world saying, ‘Go shawty, it’s your birthday. We gon’ party like it’s your birthday,'” Usher recalled.

The baby boy’s name is Sire, which is also the name of one of 50 Cent’s sons. See Usher’s full interview below.