‘I Don’t Like to be Alone’: Usher Says Being Single Is the ‘Hardest Thing’ He’s ‘Ever Had to Do’ After Highly-Publicized Break-Up with Chilli and Two Failed Marriages

Usher Raymond’s Las Vegas residency is one of the hottest tickets around, receiving rave reviews from fans and his peers alike. The R&B singer seems to have everything going for him, including a new project and a new love.

Usher makes the ladies go wild after humbly bragging about how fine he's been since the 1990s.
Usher makes the ladies go wild after humbly bragging about how fine he’s been since the 1990s. (Photo: @usher/Instagram.)

His current relationship appears to have granted him a newfound understanding of various aspects of his own self within the context of relationships. One thing that he learned is that he is, by nature, a serial dater.

“I think the hardest thing that I’ve ever had to do was be single,” he said in a recent interview with Vibe magazine.

The 44-year-old went on to elaborate on how this need to be in a romantic relationship manifested in his dating history.

“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,” he said. “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?” 

One of the most public relationships was with his then-label mate, Chilli from TLC. The two met after Usher signed with LaFace Records under L.A. Reid and dated from 2001 to 2004.

According to Chilli, one of the reasons why they didn’t work is because of the two only had “working chemistry.”

“But working chemistry does not mean it works in your personal life. If we were working, it was great, but outside of that, we’re different,” the “Waterfalls” singer said.

She also added that the two had different value systems.

“It looked great, but in real life … he knew he had to be a certain way with me and he couldn’t,” Chilli added.

She also said their split, despite the “Confessions” narrative that has floated for years, was not due to his infidelity because he never cheated on her.

In 2007, the “My Boo” recording artist tied the knot with his stylist, Tameka Foster. As a result of their marriage, the renowned “King of R&B” embraced fatherhood, welcoming two sons named Cinco, who is currently 15, and Naviyd, who is 14.

This relationship ended in 2009 in a nasty, headline-making divorce.

Within months of his divorce from Foster, Usher started dating his then-manager, Grace Miguel, who now goes by Grace Harry. The two shared a very private relationship, marrying in 2015 and divorcing in 2018.

Now, the star is enjoying moments alongside his new girlfriend, Jennifer Goicoechea. The lovebirds have been dating since 2019, according to Billboard, and together have a daughter and a son named Sovereign Bo, aged 2, and Sire Castrello, aged 1.

A little more mature, the chart-topper is not just a different type of lover, but also a different type of father. In fact, his youngest children were born; he even made a playlist to welcome the children into the world.

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