Usher has endured a ton of hardships in his life, but apparently the hardest one of them all was him being single.

The legendary R&B singer is VIBE‘s cover star for August. In a conversation published on Friday (August 4), Usher spoke about his popular Las Vegas residency, fatherhood and more – including what he feels has been his biggest life lesson.

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“I think the hardest thing that I’ve ever had to do was be single,” he admitted. “Because I don’t like to be alone. The idea of creating a life with someone is what I would like to do, maybe because I didn’t have or didn’t see that. And I get to remedy that idea by having an incredible partnership. I can then have the thing that I ultimately wanted to see. You know what I’m saying?”

Check out Usher’s VIBE cover below:

After dating TLC’s Rozonda “Chilli” Thomas in the early 2000s, Usher was married to Tameka Foster from 2005-2009 and welcomed his first children Cinco, now 15, and Naviyd, 14.

Following their split, he dated his former manager, Grace Harry, from 2009-2018. Currently, the Confessions singer is coupled up with record exec Jennifer Goicoechea, and the pair share two-year-old daughter Sovereign Bo and one-year-old son, Sire Castrello.

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In June ahead of the premiere of the new Lifetime documentary TLC Forever, Chilli opened up about her former flame and revealed that their union went on to ruin future relationships for her for years to come.

“I even stopped dating [in 2019] because before that, I thought if I met the right guy during that time that I wasn’t over [Usher] it wouldn’t work,” she told PEOPLE. “I would never want to straddle the fence.”

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Chilli also clarified that Usher’s Confessions album was not about their split, despite what many have assumed over the years because of the fact it dropped the year they broke up. “I was with him at the studio that whole time,” she explained.

Though they split in 2004, Chilli revealed she and Usher remained off and on for years and would get back together when they weren’t in other relationships – which led to her cutting off all contact with him in 2019 “to focus on myself.”

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“I love hard. I was like, ‘God, why can’t I get over this?’ He couldn’t either,” she admitted.

Chilli has since moved on, and is currently dating actor Matthew Lawrence. “I have never experienced anything like this,” she added. “He wants to be the best guy he can be and who God wants him to be. God-willing one day we’ll get married.”