Everything the Kardashian family does is put under a microscope by the media. What that means for Kylie Jenner is that everything the teenager does seems to go viral and simple things like who she dates or hooks up with quickly become public knowledge. By now Kylie realizes this, and often uses social media to create a buzz about what is she doing and with whom she is doing it with.
Kylie Jenner has been called one of the 30 most influential teens by Time magazine in both 2014 and 2015. The daughter of Kris Jenner and Caitlyn Jenner (formerly Bruce) is also the sister of Kendall Jenner and the half-sister of all the kids had Kris and Bruce had independently of one another before meeting. Kylie already owns several luxury cars and moved into her $2.7 million mansion in Calabasas, California when she turned 18.
Relationship wise, Kylie has dated several famous guys, and her most serious relationship seems to be with rapper Tyga. “I feel like I’ve been in a relationship for like, six years. I have just gone from one person to the next” Kylie told her BFF Jordyn Woods on camera. Over the years she has been rumored to have hooked up with several people, and here are 10 of those.
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10 French Montana
Rapper French Montana was a frequent subject of celebrity gossip sites and tabloids when he dated Khloe Kardashian back in 2014. The couple broke up in 2015 and Montana has also been romantically linked to actress Sanaa Lathan and fellow rapper Trina. Some rumors had it that perhaps the reason that Montana and Khloe called it quits was because the hip hop golden boy may have hooked up with Kardashian’s half-sister Kylie Jenner. Montana has been called the “King of Mixtapes” and has also dated and hooked up with many female celebrities. His debut album Excuse My French reached #1 on the US Rap and R&B charts. The chances these two actually hooked up are slim, but it may have happened.
9 Chris Brown
In late 2015 Kylie Jenner attended a Chris Brown concert in Anaheim, California. She was attacked after a fan pulled her hair which snapped her head backwards. Kylie was fortunate that security was nearby and stepped in to protect her. Her boyfriend Tyga was performing at the concert with Brown, but some rumors have had Brown and Kylie hooking up as well. Chris Brown is best known for his relationship with Rihanna which started in 2008 and ended in 2009 after domestic violence. He has also dated model Karrueche Tran and got back together with Rihanna in 2013. The rumor that Brown and Kylie hooked up is a bit far-fetched, but it could be possible.
Rap mogul Drake got into a bit of a beef with Tyga over his relationship with Kylie Jenner. Tyga called Drake a “fake” and even said that he didn’t like Drake “as a person”. Drake fired back on a mixtape where he took shots at Tyga about his relationship with an underage Kylie Jenner. Drake has been romantically linked to Nicki Minaj, Rihanna, and Serena Williams, so why not Kylie Jenner as well? Why would Drake care that Tyga was dating Kylie unless he was emotionally invested himself? This could be one well-kept hook up if Drake and Kylie ever actually got together.
7 Miles Richie
You may not have heard of Miles Brockman Richie, but rumors of him hooking up with Kylie Jenner started spreading quickly after she tattooed her initials on him. On top of that, Miles and Kylie were also seen cuddling together in a car. Miles is the son of famous singer Lionel Richie, and his sister is celebrity socialite Nicole Richie. Kylie was hanging out with French Montana and Khloe Kardashian in a recording studio in Hollywood when Miles was getting a tattoo. Kylie grabbed the tattoo gun and carved her initials into his hand, which was illegal at the time because she was only 16 and not allowed to operate such machinery.
6 Justin Bieber
Justin Bieber is one of the biggest male pop stars in the world and many female celebrities have been romantically linked to him. This guy seems to be able to get away with doing whatever he wants, and that includes hooking up with sexy celebs including Kylie Jenner. The pair was seen snuggling up at the Coachella music festival when Justin was 20 and Kylie was only 16. Bieber and Jenner claimed that they were “just friends”, but rumors of them getting together only continued on after his girl Selena Gomez unfollowed Kylie on Instagram.
5 Lil Twist
Lil Twist might not be as big of a household name as some of the other celebrities that Kylie Jenner has hooked up with. He is known for being Justin Bieber’s BFF and is a rapper signed with Young Money Entertainment. Twist was arrested in 2013 for a DUI when he was driving Justin’s Fisker Karma. In 2015 Lil Twist was arrested on several charges after he and four other people assaulted Disney actor Kyle Massey and his brother Christopher. Twist is facing 25 years in prison, so Kylie should be glad she is not dating him anymore. The two were spotted together but again claimed that they were just friends.
4 Cody Simpson
Kylie apparently dated Australian singer Cody Simpson when the two were both young teenagers in 2011. Although they never actually confirmed being a couple, they were often seen together and at one point pictures of the two making out on a rooftop were leaked. Simpson later dated model Gigi Hadid before the two broke up due to having busy schedules. Cody and Gigi were on-again off-again and she even starred in his music videos “Surfboard” and “Flower”. In late 2015 Cody confirmed that he was dating Australian model Sahara Ray. Simpson has released three albums and owns the record label Coast House Records as well.
3 Jaden Smith
Kylie Jenner and Jaden Smith were seen together in the spring of 2013 holding hands at a movie. The two reportedly dated off and on for almost a year. Just when everyone thought things were over between them, the couple was seen making out at Kim Kardashian’s wedding. Kylie commented that “Although we can’t remember exactly when we met, I couldn’t be more grateful that we did.” The son of Will and Jada Pinkett Smith has also dated the younger sister of the actress and singer Vanessa Hudgens, Stella. He even mentioned her in his song “Starry Room”, but as far as anyone knows he has never mentioned Kylie in a song.
2 Shamari Maurice
Rumors surfaced that Kylie Jenner was hooking up with a guy named Shamari Maurice after several Instagram photos were posted with captions like “He loves to cuddle w me.” Shamari is not very well known, but he is an actor who starred in the TV series Ugly Betty and in commercials for Wal-Mart and AT&T. Maurice is a close family friend and some people speculated that he and Kylie became more than just friends at one point. Shamari had a lot to gain from these rumors when he saw his number of followers on Instagram and Twitter skyrocket.
Kylie apparently first met Tyga when he performed at Kendall’s Sweet 16 party (Kylie was only 14 at the time). Tyga and Kylie made their first Instagram appearance together in the summer of 2014 around the time that he ended his engagement to Blac Chyna. Even after the couple denied the constant rumors about them dating, Tyga got Kylie’s name tattooed on his arm. The rapper even went so far as to buy Kylie a Ferrari worth $320 thousand for her 18th birthday, which is questionable seeing that he was supposedly hooking up with Kylie before she was even legal. Even without an official statement saying the two are dating, this relationship is closer to truth than just a rumor.
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