Usher confesses to how he felt about Chilli turning down his proposal.
After making headlines with his epic Superbowl Halftime Show performance and marrying his longtime girlfriend, Jennifer, the singer is speaking out about his failed proposal. Usher and Chilli dated from 2001 to 2004 and they met when he was 23 and she was 30.
“I was a young man, and she had very specific rules that didn’t work for me,” he said in a recent interview. “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.”
Although the TLC singer was questioning Usher’s love for her, that didn’t stop him from proposing to her. However, she would reject it and it would lead to them ending their relationship. He admitted that he was hurt and her rejection left him heartbroken.
“I wanted to marry her. I proposed and she told me no. I went through a great deal of pain after that,” he said. Chilli would later say in her interview that she and Usher were “on and off” after 2004. Usher claims that once the relationship ended, they remained “cool.”
“We were cool with each other, but I was very careful with that. I really did love that girl, and I was like, I don’t want to play with you. Like, ‘I can’t give you what I gave you. I did everything that I thought you would’ve wanted me to do, but I guess my good wasn’t great enough.’”
Both Usher and Chilli are in new relationships. As mentioned earlier, Usher married Jennifer Goicoechea and Chilli has been in a relationship with TV star Matthew Lawrence.