Christopher Polk/Getty Images

Usher opened up about his “first celebrity kiss” with R&B singer Monica. He also said he regrets not dating Aaliyah.

During an appearance on E!’s Daily Pop on Tuesday, March 1, the R&B crooner said he regrets not dating the late R&B princess, 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. 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.”

Fred Duval/FilmMagic

Aaliyah died in a plane crash in the Bahamas on August 25, 2001. She was 22.

The host asked Usher who he shared his first celebrity kiss with. He replied that his first celebrity kiss was with R&B singer Monica. According to Usher, she’s a pretty good kisser.

Photo may have been deleted
Sandra Rose/

Usher dated Ben Vereen’s daughter Karon Vereen when he was 15. She was a few years older than the boyish singer. Ironically, Ben was Usher’s godfather.

Usher and Karon split after he turned 16 and dropped his self-titled debut album Usher (1994).

He went on to date a slew of starlets including Monica, Brandy Norwood, Karrine Steffans, Eisha Brightwell, Rozonda “Chili” Thomas, Melinda Santiago, Joy Bryant, Naomi Campbell, and more.

Usher shares two sons with his first wife, Tameka Raymond, and two children with life partner Jenn Goicoechea. He was also married to music executive Grace Miguel from 2015 until 2018.