Prior to his appearance on Rachel Lindsay‘s season 13 of The Bachelorette this spring, and years before he found himself at the center of the Bachelor in Paradise season 4 controversy with fellow contestant Corinne Olympios earlier this summer, Jackson publicly offered his number to Spears.
On an evening in 2008, Jackson — he was in his early 20s at the time — was in the same parking lot as Spears, who was swarmed by paparazzi, and he took the opportunity to offer her his digits.
“You need a black dude! Hey, real talk. Take down my number. Take down my number,” he told Spears, who proceeded to ask his name.
“My name’s DeMario Jackson. I’m an up-and-coming actor,” Jackson, now 30, said to the “Toxic” singer in the video, obtained by E! News. “I want to be like you. I want everybody to see me on TV.”
“You’re dope,” he complimented her. “My mom loves you.”
And Jackson didn’t stop there!
“DeMario Jackson — that’s my URL — MySpace,” he continued in passing on his social media information.
As the pop singer readied herself to get into her car and leave, he didn’t pause on asking her for a hug, which she kindly obliged to.
But when he again suggested that she should “really take down” his number, Spears clearly wasn’t interested. Although her eyes were covered with dark sunglasses, her body language said it all: she turned away and made a cringed face before getting into the driver’s seat.
“DeMario Jackson — remember that!” he said as the photographers captured her driving away.
WATCH: DeMario Jackson Alleges He ‘Got Played’ on ‘Bachelor in Paradise’ — But Doesn’t Blame Corinne Olympios
Although Jackson did not return to season 4 of Bachelor in Paradise following the scandal between him and Olympios in June, he will be appearing on the BiP and Bachelorette: Men Tell All reunions shows.
“I’m doing the Men Tell All for The Bachelorette and I’ll be doing Paradise as well,” Jackson previously told TMZ. “I owe it to my cast mates. They’ve been very supportive of me throughout this whole entire thing and I want to thank them all personally, face to face — give them all hugs and bro out or sis out, or whatever. They’ve been so helpful.”
Season 4 of Bachelor in Paradise will kick off its two-night premiere on Monday, Aug. 14 at 8 p.m., and continue on Tuesday, Aug. 15 at 8 p.m., both on ABC.