DeMario Jackson Asked Out Britney Spears in 2008, & Her Response Was Hilarious

It turns out Rachel Lindsay wasn't the first woman in the spotlight who DeMario Jackson tried to woo. This X17 video shows the future Bachelorette contestant working his charm on pop star Britney Spears back in 2008. 

The video shows a brunette Britney leaving Ralphs supermarket in Los Angeles, according to Us Weekly. Several photographers surrounded the star to ask her personal questions about her kids, her relationship with then-boyfriend Adnan Ghalib and a pregnancy test. While the paparazzi searched for celebrity gossip, Jackson, who apparently was at the grocery store parking lot when Spears was leaving, used the opportunity to ask the star on a date.

DeMario made Britney laugh with this opening line: "Britney, f*** it, you need a black dude. Real talk!" Britney responded, "I need a black dude? I like black dudes. You guys are cool."

Jackson insisted that Spears take down his number. "Call me! I'm dead serious," he said. When she asked for his name, he replied, "My name is DeMario Jackson. I'm an up-and-coming actor. I want to be like you. I want everybody to see me on TV. Real talk. You're dope…My mom loves you, and she said tell Britney."

As Brit laughed, DeMario continued to confess his love for her and even began to spell out his Myspace URL (because this was a time before Instagram and Twitter handles). His confidence didn't seem to shake as he went in for a hug, asking, "Can I just have a hug for TV?" 

His friends shouted "Demo!" as Jackson, bottle in hand, pressed his luck one last time. "You should really take down my number. Like, you know what I'm saying? We should hang out," he said. 

Spears' smile faded as she got into her car with a quick "Bye, y'all," leaving Jackson to dwell in the rejection.

Things may not have worked out with Britney Spears, but DeMario's situation has only gotten worse in recent months. He was at the center of a Bachelor in Paradise sexual misconduct scandal in June, an investigation which has since been closed. This guy just can't catch a break, can he?