And her cringe after he said "you should really take down my number" is priceless.
The video (above) is from 2008 when Jackson made his move on Spears in a parking lot outside a grocery store in Los Angeles.
The video starts with Spears buying about $600 worth of groceries, then paparazzi followed her to her car where Jackson chimed in to sing her praises."
"My name's DeMario Jackson. I'm an up-and-coming actor. I want to be just like you. I want everybody to see me on TV," Jackson told Spears.
"I'm never on TV," she responded, but Jackson persisted. After saying, "Britney, I love you" and telling her his MySpace URL, he asked her for a hug.
Spears was courteous enough to give Jackson a quick embrace, but then things got awkward when he got braver: "You should really take down my number, you know what I'm saying, we should hang out."
Although she stayed silent, her facial expression screamed she wasn't interested, and she
Jackson finally got his wish earlier this year after appearing on the current season of "The Bachelorette." Viewers deemed him "the bad guy" after his supposed girlfriend confronted him on the show.
Later, Jackson's fame rose to new heights when he was at the center of Bachelor Nation's biggest controversy yet. While filming Season 4 of "Bachelor in Paradise," he was accused of sexual misconduct with fellow contestant Olympios, and the allegations briefly shut down the entire production.
No charges were filed against Jackson, and the show resumed filming a few weeks after the pair's drunken hook up concerned producers who initially reviewed the footage.