We never thought we’d ever mention Britney Spears and DeMario Jackson in the same sentence, but here we are. ICYMI, a newly resurfaced X17 video from 2008 shows a then-troubled Britney, now 35, leaving a Ralphs supermarket in LA as a very desperate DeMario, now 30, trails behind her in hopes of scoring a date with the pop diva.
In the clip (which you can watch in all its throwback glory below), the future Bachelorette star makes an advance on Britney — who was going through a public breakdown amid a painful custody battle with ex-husband Kevin Federline — as she and former manager Sam Lutfi begin packing their groceries in her car.
"Britney, f–k it, you need a black dude. Real talk!” DeMario confidently shouts as a hoard of paparazzi snap photos. "I need a black dude? I like black dudes,” a seemingly interested Britney responds. “You guys are cool.”
That’s when DeMario walks up to Britney and repeatedly begs her to “take down my number,” which prompts the “Piece of Me” singer to politely ask for his name. In a rather cringe-worthy spiel, DeMario (who was apparently once an aspiring actor) makes a failed attempt to hit on Britney by telling her he wants to “be like” her.
“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,” he tells a visibly unimpressed Brit. “My mom loves you, and she said tell Britney.”
After giving Britney his MySpace URL (because, hello, it’s 2008!), he asks for a hug — and for reasons we’ll never know, the Grammy winner obliges. "You should really take down my number. Like, you know what I'm saying?” he tells her. “We should f–king hang out.”
But a quick embrace was all Britney could take. Because after DeMario asks her out, the Crossroads actress’ friendly demeanor immediately turns into sheer fright as she shuffles away to get TF back into the safety of her white Mercedes-Benz.
The video of DeMario getting rejected by Britney comes more than a month after he made headlines for his participation in Season 4 of Bachelor in Paradise. As previously reported, he and co-star Corinne Olympios were involved in an alleged sexual encounter, which temporarily shut down production on the ABC dating show.
However, Warners Bros. found no evidence of misconduct and filming eventually resumed. Season 4 of BIP will premiere on ABC Monday, Aug. 14, at 8 p.m. EST.