and Brandy Norwood were the talk of the town when the soon-to-be NBA star took the Moesha star to his high school prom back in 1996.

Bryant was only 17 and a senior at Lowe Merion High School in Philadelphia. But while his peers were getting ready for college, Kobe was headed to do bigger things. As the nation's top-rated high school player, he was expected to be selected in the 1996 NBA Draft and go straight to the pro ranks.

Brandy was already a Grammy winner in 1996. The teen pop star had already sold more than six million copies of her debut album and was a star on the TV sitcom Moesha.

Of course, it was Kobe who asked her to be his date, and Brandy revealed the main reason why she said yes to going on a date with the high school basketball phenom.

And so she did.

Kobe was too shy to ask her out

 first met Brandy at the Essence Awards that April at the Madison Square Garden and was instantly smitten by the singer/actress. According to his mom Pamela, Kobe told her when he got home from that event that he had met a "nice, beautiful, intelligent, and sweet person." Bryant also showed a photo of Brandy from a magazine and bragged that he would take her to the prom.

But Kobe was too shy to ask her out that he asked someone else to do it for him. Luckily, that did not turn off Brandy, who only said yes after getting her mom's approval. Her mom eventually said yes and made the trip to Philadelphia with her.

Media heavily anticipated the arrival of the young power couple. Three hours after the prom started, Kobe and Brandy arrived in a white stretch limo they shared with a group. There were rumors that Brandy would sing at the event, but when reporters asked her, she said she wasn't doing it and was there to have fun. It looked as if they did.

The two became an item

After Kobe was , he appeared on her TV show, and Brandy even wore a Kobe jersey when they were interviewed. Brandy also cheered on Kobe when he won the 1997 Dunk Contest. They became an item, but in the end, Vanessa won Kobe's heart.

True to Brandy's words about her prom date, Kobe Bryant would go somewhere in life. In fact, he went from being an 18-year-old who was picked 13th in the 1996 NBA Draft to one of the greatest players to ever play in the NBA.

Aside from wearing Vanessa's ring, Kobe won five NBA championship rings with the Los Angeles Lakers. He was the 2008 NBA MVP, a two-time NBA Finals MVP, a 4-time All-Star Game MVP, and a 15-time All-NBA team selection.