Kim Kardashian Drops Bombshell: Childhood Romance with Janet Jackson’s Nephew and a Pictionary Disaster!

The reality star opened up about her longtime admiration for the “If” singer

(L) Kim Kardashian and T.J. Jackson. Photo:TheStewartofNY/WireImage; Leon Bennett/Getty

Kim Kardashian is remembering a famous old flame.

On Wednesday’s episode of The Kardashians, the reality star opened up about her personal connection to Janet Jackson as she and her friends boarded her private jet to see the legendary music icon in concert.

Dressed in the exact outfit Janet wore in her “If” music video, Kim, 44, told cameras why “Janet means so much to me, more on like a personal level, than anyone could really imagine.”

“I dated Janet’s nephew for years and years in high school,” she recalled of her relationship with TJ Jackson, adding that their romance began in junior high.

T.J. Jackson. Lester Cohen/Getty Images for Showtime/Motown

Kim also revealed that she was invited to the Jackson family’s game nights.

“One time, the entire Jackson family and me are playing Pictionary,” she began. “I was so nervous, because Janet was like, my everything.”

A bundle of nerves, she drew a “right angle” on the board — despite her word being “angel.”

“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.”

(L) Kim Kardashian and Janet Jackson. MICHAEL TRAN/AFP via Getty; Jamie McCarthy/Getty

“So she’s will always be my angle. My little angle,” Kim said with a smile.

In June 2024, Kim posted a video of herself rocking the outfit worn by Jackson in the 1993 music video for her song as she headed to see the singer in Palm Springs.

The SKIMS founder first teased part of her look on Instagram Stories as she filmed herself walking in black flared pants with fringing on the sides and black boots indoors. She then panned out to reveal her full look in a another clip where she wore a black crop top with white boning across the chest and the matching lace-up pants as “If” played.

In 2021, Kim revealed she bought the music video outfit in an auction in celebration of the singer’s 55th birthday. Julian’s Auctions later confirmed in a tweet that The Kardashians star paid $25,000 for the custom look.

“For @janetjackson’s bday bc I’m such a fan I can’t believe I won this on @juliens_auctions,” Kardashian posted on Instagram Stories at the time.

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New episodes of The Kardashians air Thursdays on Hulu.