Usher Reveals First Celebrity Crush Was Chili: ‘I Think I Was 11 or 12’

Usher fell hard for his ex-girlfriend, Rozanda "Chilli" Thomas of TLC, over a decade before the two began dating.

As one of Essence's Sexiest Men of the Moment alongside Damson Idris, the R&B icon sat down with the publication for their '60 Seconds With' segment, where he revealed that Thomas was one of his earliest crushes.

"I'ma be real honest with y'all today," he began. "My first celebrity crush was Chilli. I think I was 11, 12, something like that. Yeah."

The answer was a bit shocking, as Usher married his third wife, Jennifer Goicoechea, in February, during the weekend of Super Bowl LVIII.

Around the same time, Usher spoke to People about manifesting his relationship with Chilli, whom he dated from 2001 to 2004.

"If I am to be honest, I was her No. 1 fan, and she was my superstar," the 45-year-old said. "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.’"

But as Chilli was seven years Usher's senior, that would've made her 15 years old, which was long before she made her mainstream debut in TLC. But in adulthood, their age difference proved to be a conflict, as Usher revealed that Chill had "very specific rules that didn’t work for me."

"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," he told People.

Although Usher even proposed to Chilli in the early 2000s, she turned him down. The two have since moved on in separate relationships, with Chilli now dating actor Matthew Lawrence. Usher has been with Goicoechea since 2019 and the two share two children, Sovereign Bo, three, and Sire Castrello, two.

With his first wife, Tameka Raymond, Usher has two older sons, Usher "Cinco" Raymond V, 16 and Naviyd Ely, 15.