In a recently resurfaced X17 video from January 2008, the future reality star, now 30, approaches the pop princess, now 35, as she leaves Ralphs supermarket in Los Angeles with her then-boyfriend, Adnan Ghalib.
"Britney, f--k it, you need a black dude. Real talk!" Jackson shouts. Laughing, Spears responds, "I need a black dude? I like black dudes. You guys are cool."
After Jackson repeatedly begs the "Toxic" singer to "take down my number," he insists that he's "dead serious." She smiles and asks for his name as he replies, "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."
The future Bachelor Nation star then proceeds to give Spears his Myspace URL (throwback!) as she packs her grocery bags into the car. "Can I have a hug? Can I just have a hug for TV?" he asks before putting his arm around Spears. "You should really take down my number. Like, you know what I'm saying? We should f--king hang out."
In an instant, the Grammy winner's smile turns to a grimace as she walks away from Jackson and climbs into her car.
The video was filmed amid Spears' custody battle with her ex-husband Kevin Federline. The former couple, who were married from 2004 to 2007, share sons Sean Preston, 11, and Jayden James, 10. Spears is currently dating personal trainer Sam Asghari.
Jackson, meanwhile, recently made headlines for his brief stint on the upcoming season of Bachelor in Paradise. The ABC reality series temporarily suspended production in June after a producer filed a claim of sexual misconduct in the workplace after an alleged incident occurred on set between Jackson and fellow contestant Corinne Olympios. Jackson vehemently denied any wrongdoing, and Warner Bros. found no evidence of misconduct after completing a thorough investigation.
Season 4 of Bachelor in Paradise premieres on ABC on Monday, August 14, at 8 p.m. ET.
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