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7. Cody Simpson-
The two dated for six months back from 2011 to 2012 and their hot and steamy romance was a subject of the paparazzi. During their short romance, fans gave the pair the nickname Kody. Although the two never went public with their relationship, it was evident to see how in love and happy they were when photos of the pair hugging and kissing surfaced in the media. However, the happiness didn’t last long and the pair unexpectedly split. It wasn’t until 2014 that Simpson finally opened up about his relationship with Kylie when he guest-starred on Ross Matthews show, “Hello Ross.” While the singer didn’t reveal the exact cause of the breakup, he did hint that the romance fizzled out because of the letter “K.”
6. Jaden Smith-
Rumors Kylie and Jaden started swirling around Hollywood in early March and the two dated for a couple of months back in 2013. Their romance was quickly documented by the tabloids, and even the two never addressed their relationship, it became evident that they were dating when they were spotted walking out of a movie theater holding hands. The lovebirds finally confirmed their relationship when Kylie appeared in Jaden’s music video “Blue Ocean.” Jaden even attended Kim and Kanye’s grand wedding. The couple was on and off for a year before finally breaking up for good in 2014. While neither of them cited a particular cause for the breakup, many rumors contributed to the split which includes jealousy, cheating and apparently Will and Jada urging Jaden to leave Kylie in fear that Kylie was using him for fame.
5. Miles Richie-
The duo made headlines after Kylie, and Lionel Richie’s son Miles were caught on video hanging out at a recording studio. In a video obtained by the press, Kylie is clearly seen illegally tattooing a male who was reportedly Miles. Kylie was only 16 years old at the time of the incident, and it was rumored that she was tattooing her initials on his arm. Even though many reports stated her and Miles were just pals, friends don’t tattoo each other’s names on their bodies. And they also don’t make out in public. Nevertheless, the pair didn’t last long as they only dated for two months back July 2014 before calling it quits later that year in September.
4. Justin Bieber-
Singer Justin Bieber has been a close friend of the Kardashian family for years, and he is especially close with Kendall and Kylie. Their close friendship sparked rumors of a possible romance between him and the reality star. However, two are quick to shut it down stating that their friendship is similar to a brother and sister type. But fans were trying to uncover if this was genuine or if they were trying to hush up the media. Kylie’s and Justin’s close friendship even made Justin’s ex Selena Gomez jealous that she went as far to delete the photos of her and the Jenner sisters together at Coachella.
3. A$AP Rocky-
Nonstop rumors of a hushed romance started circulating in late November 2015 after Kylie was seen with rapper A$AP Rocky. They were leaving a club and paparazzi followed them home. It left many of us wondering what happened behind closed doors but the rumors were addressed as the two claimed they were just friends. At the time, Kylie was flying solo, with no Tyga insight so fans couldn’t help but think if there was something else going on. The two partied a Hyde nightclub on the Sunset Strip in WeHo before heading leaving at 2 a.m.
Tabloids and the media searched for answers as an alleged romance was happening with the reality star and rapper PartyNextDoor in early 2016. During this time, Kylie and Tyga briefly split a few months ago, and many fans wondered if she had a new boy toy. For months, the two were spotted hanging out together and were captured bowling and even attending Drake’s house party together. Even though Kylie and PartyNextDoor tried to keep their relationship quiet, they confirmed their relationship when Kylie appeared in his new music video, “Come and See Me.” In the video, the rapper and Kylie share a passionate kiss in the rain. However, this new found love didn’t last long, and they went their separate ways after being together for two months.
The two first met back when Kylie was fourteen, but they didn’t get romantically involved until she was 17 years old. Relationship rumors first circulated back in September 2014, and at first, both of them denied that they were dating especially since their age gap and Kylie being under 18 years old was frowned upon. Eventually, the two couldn’t evade the media after they were spotted hanging out frequently and Tyga was even spotted with Kylie’s name on his inner arm. Since their relationship has been public, the two have encountered some issues. Which includes allegations of cheating, rumors of a possible engagement and even breaking up a few times before getting back together. Even though Tyga is Kylie’s main squeeze, for now, we’ll see if that statement sticks a few years down the road.