Kylie Jenner, Tyga, and Blac Chyna
Tyga and Blac Chyna began dating in 2011, and the pair had a son together before breaking off the engagement in 2014... but rumors of a romance between Kylie Jenner and Tyga also started in 2011 when the artist performed at Kendall Jenner's sweet sixteen. It wasn't until right after Kylie turned 18 that the couple became official. These days, the on-again-off-again couple shares a daughter together.
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