Usher Recalls 'Pain' Of TLC's Chilli Rejecting His Marriage Proposal: '[It] Broke My Heart'

Usher has opened up about his previous relationship with TLC‘s Chilli, revealing that the two split after she turned down his marriage proposal.

In an interview with PEOPLE magazine, the R&B legend spoke on his early romance with singer Rozanda “Chilli” Thomas and the “pain” of their split.

Describing himself as someone who was “always charming the older ladies” and confessed his love for the TLC star, who is seven years his senior, in 2001, Usher admitted that he had been lusting after her for years and had a poster of her in his room when he was growing up.

“At the age of eight, I put her poster on my wall and said, ‘Man that girl is so beautiful. One day I’m going to meet her,'” he recalled.

After dating for three years, the two reportedly split due to differing priorities. The Super Bowl headliner admitted that their breakup put him through an immense amount of pain and trust issues for years afterwards.

“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 said.

The “Waterfalls” singer spoke candidly about her relationship with Usher last year, admitting that their split ruined her future relationships.

“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 said. “I would never want to straddle the fence.”

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Although the two split in 2004, Thomas admitted to them being on and off for years until she finally cut off contact with Usher in 2019.

Despite the difficulties of their relationship, Usher added that they’ve remained friendly with one another. “I’m not hurt over that at all, we’ve since become cool with each other, celebrate each other and it’s always light when we see each other,” he explained.

Usher tied the knot this past weekend with music executive partner Jennifer Goicoechea, reportedly cementing the union at a private ceremony in a drive-thru service in Las Vegas following his Superbowl Halftime show.

Speaking on his love for his now-wife, the “Yeah!” hitmaker told PEOPLE: “I have an amazing partner, a support system. We have an amazing dynamic between our relationship where I’m able to be passionate still about what I do and have an incredible partner to work through some of the harder times as a young man dealing with children and dealing with the dynamic of how you communicate with them.”