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.
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