In a new candid interview, Usher told it all about his past relationship with TLC’s, Chilli, and how their split had a major impact on his trust in women. The R&B crooner shared his personal journey, shedding light on the pain he endured and the valuable lessons he learned.

In his interview with People, Usher explained that his love story with Chilli began in 2001, when they started dating. The seven-year age gap didn’t deter their connection, and Usher expressed his admiration for her, stating, “If I am to be honest, I was her No. 1 fan, and she was my superstar.”

Their relationship was crazy intense. Usher even dropped a bombshell, revealing that he went as far as proposing to Chilli, hoping to spend the rest of his life with her. However, to his surprise, she crushed him when she turned down his proposal. Chilli’s rejection shattered Usher’s heart:

“I wanted to marry her. I proposed and she told me no. I went through a great deal of pain after that, not trusting women or wanting to open up.” He admits, “I hurt her too,” but the situation “broke my heart.”

Reflecting on this painful chapter of his life, Usher acknowledged the specific rules and expectations that Chilli had, which ultimately didn’t align with his own desires. He revealed:

“We were missing each other. I really did want to have a different type of relationship where she was there with me, and she couldn’t be. She didn’t believe that I was actually in love with her as much as I was.”

Chilli previously confessed that while she and Usher had an on-again-off-again-relationship for years after their official break-up, their relationship expectations of each other became too mush for her, she stated:

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

The aftermath of their breakup was tough for Usher. He confessed that he struggled to trust and open up to women after dating Chilli. The experience not only hurt Chilli, but also caused Usher to question his own worth and capabilities in relationships.

Despite the pain, Usher says he and Chilli managed to find common ground and maintain a cordial relationship over the years. While they celebrated each other’s successes, they both understood that their romantic connection was no longer pursuable. Usher said:

“We’ve since become cool with each other, celebrate each other, and it’s always light when we see each other.”

Today, Usher has found love again. As we previously reported, he recently jumped the broom with his longtime girlfriend, Jenn Goicoechea, during the Super Bowl LV!!! weekend, where he performed the Halftime Show. Though the scars of Chilli stomping on his heart, so to speak, have passed, Usher has grown from his experiences.

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