Brandy has broken her silence about the death of Kobe Bryant, who had taken her to his high school prom more than 20 years ago, and weeks before he was drafted to the NBA.

The retired Los Angeles Lakers star, one of the most popular and successful basketball players of all time, died at age 41 in a helicopter crash on Sunday along with 13-year-old Gianna Bryant, one of his and wife Vanessa Bryant's four daughters, and seven other people, including two other teenage girls.

"Never will I understand," Brandy, 40, wrote on Instagram on Friday, alongside an image of Kobe hugging Gianna. "My condolences to @vanessabryant , the entire family, and all in pain during this tragic time. Love ♥️ #Mamba #Mambacita."

In May 1996, at age 17, Brandy, a rising R&B singer and star of the hit sitcom Moesha, was Kobe's date to his Lower Merion Township High School prom at the Bellevue Hotel in Philadelphia. Brandy wore a sleeveless champagne Moschino dress and watching shawl and her signature long braids. Kobe, almost 18 at the time, wore a black tux and banded-color shirt with no tie.

"He asked me to go to the prom with him, and since he was a nice guy...I asked my mom, and she said yes," Brandy told the New York Daily News at the time.

"I said I don't know this guy. I had no idea who he was," Brandy's mother, Sonja Norwood, told the Philadelphia Daily News in 1996. "And then Brandy said, 'He's a basketball player.' And I said, 'So?'"

Brandy, Kobe Bryant

Bruce Cotler/Globe Photos/ZUMAPRESS.com

"I liked that he had involved parents and he was doing well academically," she added. "He seemed to be a pretty good kid. He was levelheaded and grounded. And I said OK."

Kobe had long had a crush on Brandy.

"We were in English class together, and he had one of those teen magazines and it had a picture of Brandy because she was on that show, Moesha," one of the basketball star's friends and classmates, Ashley Pietropaolo, told the newspaper. "He showed me and he said, 'I'm gonna bring this girl to prom.' And I was like 'Whatever, you're crazy.' Every day, he would be like 'I'm bringing this girl to prom.'"

Brandy and Kobe finally met months prior to the event at a recent Nike All-Star basketball game in the city, the Philadelphia Inquirer had reported.

Brandy, Kobe Bryant

Mirek Towski/DMI/The LIFE Picture Collection via Getty Images

The two kept in touch. Brandy even got him a guest spot on Moesha that year. In June, a month after the prom, the two attended the premiere of the Arnold Schwarzenegger film Eraser in Los Angeles. Two weeks later, the Charlotte Hornets selected Kobe with the 13th overall pick in the first round of the NBA draft.

He was immediately traded to the Lakers, where he would spend his 20-year career. He retired from the NBA in 2016.

In 2016, Brandy told TMZ that she kept the prom dress.

"It was a special night," she said.

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