Kylie Jenner’s Dating History Is More Complex Than Any of Her Sisters

Of the five Kardashian-Jenner sisters, Kylie Jenner’s dating history is the most complex. Sure, sisters like Kendall Jenner and Khloé Kardashian have had more obscure NBA boyfriends, but there’s something about Kylie’s relationship past that seems much more interesting. Perhaps it’s because she’s the youngest of the Kardashian-Jenners, and therefore is the most public about her relationships. Of the sisters, Kylie has probably posted the most her boyfriends on Instagram. Heck, she even confirmed when she and Travis Scott broke up (more on that later) in 2019 days after the news broke.

But before we dive into Kylie’s ~celebrity~ boyfriends, let’s look back at the first-ever BF we know of: a man named Ramsey IV. According to Cosmopolitan, Kylie and Ramsey...

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