One Of Kim Kardashian's First Boyfriends Was A Part Of This Famous Family

Kim Kardashian has a star-studded romantic history. Long before she filed for divorce from her husband Kanye West and jumped into a new relationship with comedian Pete Davidson, Kim had an A-list dating roster. The "Keeping Up With The Kardashians" star has been married a total of three times, as she famously called off her second marriage to NBA player Kris Humphries after 72 days in 2011.

Kim entered her first marriage when she was only 19 to music producer Damon Thomas. The Skims mogul revealed on "KUWTK" that her first trip down the aisle was admittedly done under the influence. "I did ecstasy once, and I got married," she said on an episode. "I did it again, I made a sex tape. Like, everything bad would happen." The tape Kim is referring to was infamously made with her boyfriend at the time, rapper Ray J. The reality star has also been romantically linked to footballer Reggie Bush, entertainer Nick Cannon, and 98 Degrees singer Nick Lachey for a short fling, per Access.

It turns out, Kim Kardashian's dating history with fellow celebs extends to her high school days — and one of her first boyfriends was a part of one of America's most famous families.

Kim Kardashian dated Michael Jackson's nephew T.J. Jackson when she was a teenager. According to Showbiz Cheat Sheet, Kim was about 14 when she began dating Tito Jackson's son, who was two years her senior.

A former nanny of the Kardashians spoke highly of T.J. when the two teens were together in the book "Scandal Made Me Famous." "I really liked T.J.," nanny Pam Behan said, per People. "He was kind of on the quiet, shy side, always very nice and polite. A good-looking kid, and as far as I could ever see, he treated Kim with great respect." Kim told the publication in 2009 that her relationship with T.J. brought her to his famed uncle's home on different occasions. "That was the most magical place on earth," she said. "I had my birthday at Neverland Ranch. Who else can say that?"

It has also been speculated that T.J. was Kim's first intimate experience. "When I did want to have sex the first time I was almost 15," she said in an interview with Oprah Winfrey in 2012, per Glamour. The star opened up about talking to her mother Kris Jenner about the big step. "She was like, really open and honest with me," Kim explained.

While the romance between teen Kim Kardashian and T.J. Jackson wasn't built to last, both stars have been complimentary of each other's families throughout the years. On an episode of "The Jacksons: Next Generation," T.J. revealed that he was close with Kim's mother Kris Jenner. "Kris was an important person for me when I lost my mother," he said. "I was dating Kim at the time and spending a lot of time with Kim and her family, so Kris was like a mother to me."

Kim has also spoken highly of the Jackson family in the time since she fell for her high school beau. The reality star sent her condolences the family's way when Michael Jackson died in 2009. "I love u Jackson family, my prayers are with the whole family!" she tweeted.

Kim recalled a hilarious moment she shared with the Jackson family on a 2015 episode of "Keeping Up With The Kardashians." "I was playing Pictionary when I was 15 years old with the entire Jackson family—including Janet," she recalled, per Bustle. In her story, Kim described the mortifying mistake of misspelling "angel" as "angle." She said the Jacksons pitied her in the moment, saying, "We'll give you the point, we feel so bad for you,'" she added, "I literally wanted to die."