Nearly 20 years after he and TLC’s Rozonda Thomas (aka Chilli) broke up after three years of dating, Usher reveals how the split led to him not trusting women.
During an interview with PEOPLE, Usher spoke about dating Chilli, who is eight years his senior. “I was always charming the older ladies,” he explained. “If I am to be honest, I was her No. 1 fan, and she was my superstar. At the age of 8, I put her poster on my wall and said, ‘Man that girl is so beautiful. One day I’m going to meet her.”
Although the relationship worked for three years, Usher admitted that Chilli had specific rules for him that just didn’t work. “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.”
The Confessions hitmaker revealed he ended up proposing to Chilli. However, she turned him down. “I went through a great deal of pain after that, not trusting women or wanting to open up,” he said.
Usher noted that while he hurt Chilli in the situation, it left him brokenhearted as well. Chilli previously said her relationship with Usher remained off-and-on for years. But he confirmed that for him things ended at their breakup. “We were cool with each other, but I was very careful with that,” he continued. “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.’”
Usher States He’s Not ‘Hurt’ Over His Breakup With Chilli Anymore
As he continued to reflect on his relationship with Chilli, Usher stated he was no longer hurt that he and the TLC bandmate couldn’t work things out.
“We’ve since become cool with each other,” Usher noted. “Celebrate each other and it’s always light when we see each other.”
Following his relationship with Chilli, Usher moved on to Tameka Foster. He had two children, Usher “Cinco” Raymond V and Naviyd Ely Raymond, with Foster before they split up in 2009. He married Grace Miguel in 2015 and then divorced her in 2018.
In October 2019, Usher started a relationship with music executive Jennifer Goicoechea. They had a daughter in September 2020 and a son in September 2021. The couple got married in Las Vegas on Feb. 11 of this year. This was also the same day that he performed at the halftime of Super Bowl LVIII.