Usher Reflects on the 'Hurt' of Stepson's Death: 'It's a Real Hard Thing to Lose a Child' (Exclusive)

The Super Bowl halftime headliner opens up to PEOPLE about the devastating loss his family and ex-wife Tameka Foster suffered years ago

Usher and his family know about true, unthinkable heartbreak.

The star, 45, tells PEOPLE about that and more in this week's cover story, where he opens up like never before about his ups and downs in the spotlight.

Back in 2012, Usher and ex-wife Tameka Foster, 53, learned that her son Kile, 11, (with ex-husband Ryan Glover), was the victim of a tragic boating accident.

"I received the call back then, she was in Italy at the time, and I chartered a private plane to get her home as fast as I could because she was just so distraught," he recalls of being there for Foster, who he'd divorced in 2009 after two years of marriage.

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Related: Usher's Ex-Wife Tameka Foster Asks Georgia Officials to Drain Lake Where Her Son Died in Jet Ski Accident

"We were not even together at the time. But I was like, 'Okay, let me try and be of help to her and help her as much as I possibly can'. It's a real hard thing to lose a child."

For his part, "It hurt me," he says. "Kile was an amazing child. For the time that he was here, he was a great influence. There's not a day that his brothers and his mother don't think about him."

He and Foster share sons Usher V, 16, and Naviyd, 15. As for their current co-parenting relationship, “I’m not going to lie, we have more difficult days than we have great ones,” Usher says.

Related: Usher Opens Up About Co-Parenting While Raising Child with Type 1 Diabetes: 'It Is Very Complicated' (Exclusive)

In 2013, Usher V, then 5, nearly drowned in the singer’s pool. “That was one of the hardest days of my life,” he says, “and I’m certain one of the hardest days of hers.”

He adds, "To know that I would have a similar situation that could have just taken my son's life. It's like I understand and have great empathy for what both her and Ryan, her ex-husband, had to deal with because I've experienced a portion of it in real-time."

He and Foster were already in the middle of a long custody battle, and the scary incident exacerbated tensions before a judge found that there was no negligence on his part. Says Usher: “I love my boys, and I would never do anything to compromise or endanger them.”

These days, “we are raising our sons together,” he says of partnering with Foster, who stars on WE tv's new reality show Bold & Bougie. “It’s a process, he adds, but "we’re doing our best.”

For more on Usher's life and loves pick up this week's issue of PEOPLE, out Friday.

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