In this week’s DIVA Dating Digest, we have a look at the relationship timeline of this legendary rapper and CEO 


Brat and Judy are practically American royalty at this point. Da Brat rose to her legendary status as a rapper when she released her debut album Funkdafied in 1994. Selling over one million copies, she became the first female rap act to receive a platinum certification. 

While Da Brat was busy in the studio, her wife Jesseca “Judy” Dupart was busy forming her hair product empire. As the CEO of beauty and haircare brand Kaleidoscope, Judy is the proud founder of a multi-million dollar company. 

Together, they are quite the power couple. But how did they meet? In this week’s DIVA Dating Digest, we give you the lowdown. 

2017: The pair met at an event for Jesseca’s haircare company

When Jesseca hosted a Kaleidoscope brand event, she probably wasn’t expecting to meet the love of her life. But when Da Brat entered the room, everything changed. “I was real nervous and scared at first. I would hide behind furniture when she would talk to me,” the rapper said in a 2021 episode of Growing Up Hip Hop Atlanta. 

Their first date didn’t quite go to plan, however, as it became apparent the pair weren’t quite on the same page. While Da Brat thought they were meeting up for a date, Jesseca thought it was all business. Yikes. 

March 2020: The couple confirmed their relationship publicly 

After taking it slow, Da Brat and Jesseca went public in an iconic Instagram post. Showcasing the Bentley that Jesseca had got her for her birthday, Da Brat hard launched their relationship. “Never have I EVER. Needless to say… I’ve always been a kind of private person until I met my heart’s match who handles some things differently than I do,” the rapper wrote in a comment. 

“Thank you baby @darealbbjudy for far more than this incredible birthday gift. I have never experienced this feeling. It’s so overwhelming that often I find myself in a daze hoping to never get pinched to see if it’s real so I can live in this dream forever. SEE @darealbbjudy page for the BEST SURPRISE EVER‼️ #sosoblessed #twinflame #isthismylife #dontwakemeup #nothinghappensbyaccident” 

August 2021: The couple get their own show – Brat Loves Judy 

Just when this couple couldn’t get any more iconic, they signed a deal with WeTV for their own reality TV show called Brat Loves Judy. In this show the couple pulled back the curtain on their extraordinary life and relationship, letting viewers see their love openly. Audiences everywhere fell in love with their amazing love story! 

February 2022: The pair tie the knot 

Da Brat and Jesseca had a fairytale wedding in Georgia, with stars like Eva Marcille, Porsha Williams and Kandi Burruss in attendance. Arriving in horse-drawn carriages, the pair walked down the aisle to Here And Now by Luther Vandross. Their wedding date (2 February) was especially important to them. 

“We’ve been calling each other twin flames for a while. So this date, 2/22/22, is a significant event. We just didn’t want to miss it because it comes once in a lifetime,” Jesseca told PEOPLE magazine at the time. “It’s relevant. It’s just real significant to our relationship. It signifies angel numbers, and it also is reminiscent of twin flames.”

July 6, 2023: The pair welcomed their son True Legend into the world 

Earlier this year, we saw the couple welcome the new addition to their family into the world. Showcasing their beautiful son, Da Brat told PEOPLE magazine: “I cry every day. I just look at him and boo-hoo, because I’m so grateful.”

We can’t wait to see what this couple do next! 

DIVA magazine celebrates 29 years in print in 2023. If you like what we do, then get behind LGBTQIA media and keep us going for another generation. Your support is invaluable. ✨

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