16) Tyga
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Tyga has a history of quite popular relationships, especially in music and entertainment. His most famous relationship recently was with reality television star Kylie Jenner, whom he dated from 2014 until she was 17, which lasted until 2017.
Before dating Jenner, Tyga dated singer Blac Chyna; he fathered a son named King Cairo. This rapper has also dated models, including Demi Rose and Iggy Azalea.
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