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Can You Guess Which of the Kardashian-Jenner Sisters Has Dated the Most Rappers?

Gettyimages | Tommaso Boddi
By Zachary Holt

The Kardashian-Jenner sisters have all had their fair share of dating celebrities which have included the likes of NBA stars, athletes, models, musicians, and especially rappers.

While it may be difficult to backtrack and come up with all the rappers and hip-hop stars that the sisters have dated over the years, we have them right here and which one has been with the most throughout their lives. Which one do you think has dated the most? Read on to find out.

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Kim Kardashian (3)

Gettyimages | Dimitrios Kambouris

Starting out with Kim Kardashian, everyone is aware that she's currently married to Kayne West, one of the biggest names in the game. The two have four children together, North, Saint, Chicago, and Psalm. The two have been together for seven years, as they first started dating back in 2012.

Perhaps one that doesn't come to mind, though, is her relationship with Nick Cannon. This relationship didn't last very long, as the couple only dated from 2006 to 2007. The 'Pray for Him' rapper called quits when he felt as though he couldn't trust her anymore.

In speaking with Howard Stern, he revealed, "If she might have been honest with me, I might have tried to hold her down and be, like, ‘That was before me,’” Cannon shared about Kim’s infamous sex tape with Ray J. “She’s actually one of the nicest people you’ll ever meet. But [it’s] the fact that she lied and told me that there was no tape."

Which brings us to the other rapper she was with for some time, Ray J.

Khloe Kardashian (1)

Gettyimages | Ethan Miller

Although Khloe Kardashian is more known for pursuing NBA stars like Lamar Odom and Tristan Thompson, she also had a brief stint with the rapper French Montana. The relationship didn't last for very long and in 2014, the couple split.

There wasn't any bad blood between the two and ended on good terms. French Montana spoke with Haute Living, explaining that Khloe and himself are still good friends and everything ended on a good note.

"Me and Khloé are always going to be friends, and the family still remains close,” the rapper shared. “I feel like we had a real dope relationship–there was no bad blood, nobody did something to somebody that we couldn’t come back from. The love was real. When the love was like that, it’s always going to be like that."

Kylie Jenner (5)

Gettyimages | Steve Granitz

Kris Jenner's youngest daughter, Kylie Jenner, has also had a slew of rappers that she has fancied and dated over the course of the years. Her first, though, was Tyga. The 'Rack City' rapper and Kylie began dating in 2014; however, that relationship would not stand the test of time.

Soon afterward, Jenner was dating another rapper. This time, though, it was ASAP Rocky. To Kylie, her relationships haven't seemed to make it out of the initial stages as she also had flings with Stitches and Party Next Door. Jenner would soon rekindle the romance with Tyga in 2017, but it would not last.

Her most recent relationship with a rapper was Travis Scott. The two have a child together but split up after Kylie wanted to settle down and have more children. Scott was about to go on tour and did not share the same sentiments. Currently, the two are working through co-parenting their child.

It's also been rumored that Kylie and Drake have been getting cozy, but we can't confirm that at this point.

Kendall Jenner (2), Maybe?

Gettyimages | Pierre Suu

The second youngest daughter, Kendall Jenner, has been known to keep her relationships on the down-low, but it hasn't stopped her from being rumored to dating a couple of rappers, herself. Ironically, those two also happened to have previously dated her sister: ASAP Rocky and Travis Scott.

Whether or not those rumors are true, we don't know. Kendall has kept her dating life secret for most of her life.

The only Kardashian-Jenner sister that has not yet had a relationship with a rapper is Kourtney. Although she has been with models and other high-profile people, she has yet to date a rapper, at least for now.

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