WATCH: Britney Spears Brutally Rejected DeMario Jackson’s Request for a Date in 2008

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Even before he was on The Bachelorette, DeMario Jackson was already trying to date his way to fame.

In a recently unearthed paparazzi video from 2008, the Bachelor in Paradise star was seen trying to hit on Britney Spears in front of a Los Angeles grocery store. While packing her car with shopping bags with then-boyfriend Adnan Ghalib, the singer was approached by DeMario — who offered his Myspace URL and begged Britney for a date.

“Britney, f**k it, you need a black dude. Real talk!” he shouted.

“I need a black dude? I like black dudes,” the pop princess quipped. “You guys are cool.”

Though Britney was happy to make small talk, she wasn’t too thrilled when DeMario started harassing her with requests to take down his number to hang out.

“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,” the future reality star said. “Can I have a hug? Can I just have a hug for TV?”

He added, “You should really take down my number. Like, you know what I’m saying? We should f**king hang out.”

The request was met with an awkward embrace and an equally cringe-worthy handshake. Grimacing, Britney then hopped into her car as her companion stopped DeMario from following her to the driver’s side window.

The video was filmed when Britney was in the middle of a custody battle with ex-husband Kevin Federline. She is now Sam Asghari, a model who appeared in her “Slumber Party” music video.