Kim Kardashian’s Secret Jackson Family Connection, Her Mystery Date Revealed

Kim Kardashian has always been open about her love for Janet Jackson, but as it turns out, her connection to the music legend runs deeper than just fandom.

On Wednesday’s episode of "The Kardashians," as Kim Kardashian and her friends boarded her private jet to see Janet in concert, she opened up about why the pop icon holds such a special place in her heart.

“Janet means so much to me, more on like a personal level, than anyone could really imagine,” she told the cameras while dressed in an exact replica of the outfit Janet wore in her If music video.

Then, she dropped the unexpected dating bombshell. “I dated Janet’s nephew for years and years in high school,” she revealed, referring to TJ Jackson. Their romance, she explained, actually started back in junior high.

Kim’s connection to the Jackson family didn’t stop with her teenage romance. She was even invited to their legendary family game nights, although she admitted that one particular night left her mortified.

“One time, the entire Jackson family and me are playing Pictionary,” the now 44-year-old recalled. “I was so nervous because Janet was like, my everything.”

Caught up in the moment, Kim completely flubbed her turn, mistakenly drawing a “right angle” on the board instead of something related to her actual word, “angel.” Luckily, the Jacksons were kind about her nerves. “Jermaine came up to me afterwards, and was like, ‘Baby girl, the word was ‘angel,’ but I felt so bad for you that we’re gonna let you have this point,’” she laughed. “I wanted to melt.”

The moment clearly stuck with her, as she jokingly concluded, “So she will always be my angle. My little angle.”

Kim Kardashian's admiration for Janet Jackson has been no secret, and she took her fandom to the next level at the singer’s Palm Springs concert in June 2024. Kardashian attended the show wearing the exact outfit from Jackson’s iconic “If” music video, a look she had purchased at auction in 2021 for a cool $25,000 in honor of Janet’s 55th birthday.

The 44-year-old reality star turned business mogul, and aspiring lawyer made quite the statement, donning the famous black crop top and bell-bottom pants ensemble. Kardashian, along with sister Khloe Kardashian and mom Kris Jenner, attended the Rock and Roll Hall of Famer's concert, where they were seen dancing and singing along to hits like “Again” from the "Poetic Justice" soundtrack.

Kardashian originally won the outfit at Julien’s Auctions, where over 800 items from Jackson’s career were sold. At the time, the pop legend even acknowledged Kardashian’s purchase, responding to her Instagram Stories with, “Thank u so much @kimkardashian. I hope ‘If’ gives u as much pleasure as it did me.

Kim's influence on fashion extends beyond her own wardrobe.

Her shapewear and loungewear brand, SKIMS, has become a powerhouse in the industry, known for its inclusive sizing and focus on comfort and style. SKIMS' success has been driven by Kim’s ability to tap into current trends while also setting them, blending practicality with a sleek, minimalist aesthetic that aligns with her personal style.

She's also known for her memorable fashion moments, like wearing Marilyn Monroe's iconic dress at the 2022 Met Gala or showcasing vintage and archival pieces, as she did with Janet Jackson's "If" music video outfit.

Launched in 2019, SKIMS quickly gained popularity for its focus on inclusivity, comfort, and body positivity. The brand offers an extensive range of sizes and a diverse palette of skin tones, catering to a wide array of body shapes and shades.

Initially, SKIMS started as a shapewear brand, but it has since expanded into everyday essentials, including bras, panties, loungewear, swimwear, and even menswear. The brand's product lines often sell out quickly, thanks in part to Kardashian's massive influence and savvy marketing, which often includes campaigns featuring real people and diverse models.

New episodes of "The Kardashians" are available to stream on Thursdays on Hulu.