Usher dropped by E!’s Daily Pop to promote the second leg of his Las Vegas residency. During the interview with Daily Pop correspondent Francesca Amiker, the two played a game inspired by his 2004 studio album, Confessions.

Amiker asked the chart-topping artist if there was a celebrity he wished he had the chance to date.

“I’ve never told anybody this, but I’m going to give you an exclusive,” Usher said. “Somebody that I was really good friends with that I wish I would have taken more serious because she was a really, really close friend of mine for a small amount of time,” he continued, revealing his dream crush was the late Aaliyah.

“And then we just kind of disconnected,” he added.

The “U Got It Bad” singer divulged his regrets about not dating Aaliyah before the “Rock the Boat” singer tragically died in 2001 in a plane crash.

Unleashing more secrets, Usher shared that R&B singer Monica was his first celebrity kiss. “She’s a good kisser,” he said.

Now, Usher is in a relationship with Jenn Goicoechea, who gave birth to their second child in September. Usher, who was in charge of the music during his wife’s delivery, said that his son was welcomed into the world by the breakout hip-hop hit “In Da Club” by 50 Cent.

Usher and 50 Cent both coincidentally named their sons Sire, with the singer admitting that 50 Cent was entirely on board with the name-sharing.

“Me and 50, we talked about it, and it felt really cool to introduce him to the world saying ‘go shawty it’s ya’ birthday, we’re gonna party like it’s your birthday,” Usher said.

Usher is now the father of four children: Sire Castrello, daughter Sovereign Bo, 1, son Naviyd Ely, 13, and son Usher V, 14.

Despite being a megastar, Usher said his children don’t view him as a cool dad, even though he’s tried to convince them otherwise. However, the R&B crooner welcomes the dissociation from his life in the public eye and his family time.

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