1. Cody Simpson 

Kylie and Cody dated when they were just early teens in 2011, and although they never blatantly confirmed their coupling, it was pretty obvious that they were a thing. Recently, pictures of the two making out leaked, proving that everyone’s assumptions were true.



2. Jaden Smith

Rumors of Kylie and Jaden’s relaysh first started back in the spring of 2013, but it wasn’t confirmed until a few months later when they were seen holding hands coming out of a movie. The pair was on and off for about a year, and just when people thought they were officially done, they were apparently seen making out at Kim Kardashian’s wedding in May 2014. Ah, young love!


3. Lil Twist

Just says after Kylie and Jaden were seen jewelry shopping together, she was spotted out and about with Justin Bieber’s BFF. No one knows what really went down with these two, but our guts are telling us that they were just friends.

3a3b3c3d4. Shamari Maurice

At the beginning of the summer, Kylie posted numerous Instagrams with Shamari with captions like, ‘He loves to cuddle w me.’ As expected, this led to many dating rumors and questions about if she and Jaden were really dunzo.



5. Justin Bieber

Every time Justin and Kylie are seen together, there seems to be countless dating rumors. But the gossip really heated up recently when Selena unfollowed the youngest Jenner on Instagram shortly after she and JB seemed to be getting too close for comfort. Yikes…




6. Miles Richie

Kylie and Miles made headlines when she tattooed her freakin’ initials on him (which was illegal, btw)! Shortly after that shocker, the pair was photographed cuddling in a car, leading to inevitable dating rumors.



6. Tyga



8. Travis Scott