14. Tyga & Kylie Jenner
We always thought that it was kind of weird that Tyga was hanging around Kylie Jenner when she was only 16 and 17 years old. Especially after his split with Kim Kardashian‘s close friend Blac Chyna, in which the two share a child. What’s even crazier is that Chyna is now pregnant with Rob Kardashian‘s child. Talk about keeping it in the family… Anyway, after two years of dating, Tyga and Kylie Jenner decided to call it quits in May 2016. Things got really strange when reports came up that Tyga was involved in with a transgender woman. A couple days after the two split, Kylie was spotted with rapper, A$AP Rocky and later singer, PartyNextDoor. Tyga was also spotted with a new girl. But the funny thing about their break up is that supposedly the two are back on good terms and trying to rebuild their relationship. Let’s see how long this lasts…
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