<p id=”par-1_66″>The Kardashian and Jenner sisters are known for <a href=”https://www.cheatsheet.com/news/khloe-kardashian-fans-pleading-for-her-to-stay-away-from-nba-players.html/”>their high-profile romances</a>. Some are a lot more open about their romantic lives than others, though. Kendall Jenner is by far the most private of the five sisters, but she’s still had a few major romances. For example, she has seriously dated Bad Bunny and Devin Booker in recent history, but do you know which relationship lasted longer?</p>
<h2 class=”wp-block-heading” id=”h-kendall-jenner-went-public-with-devin-booker-in-2020″>Kendall Jenner went public with Devin Booker in 2020</h2>
<p id=”par-2_69″>Kendall Jenner and Devin Booker were first spotted together in April 2020, when they road-tripped from California to Arizona. Fans were quick to assume the pair were dating, though they denied early reports. They were spotted together several more times, making it clear they were a couple, but <a href=”https://www.cheatsheet.com/news/kendall-jenner-not-labeling-her-relationship-with-devin-booker.html/”>they refused to confirm</a> anything. In February 2021, they finally went Instagram official. In June 2021, they celebrated their first anniversary.</p>
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<p id=”par-3_97″>Things between Devin Booker and Kendall Jenner seemed to be going pretty well. At the very least, the relationship seemed mostly drama-free. That eventually changed. While Booker accompanied his girlfriend to Kourtney Kardashian and Travis Barker’s wedding in Italy, the pair stopped seeing each other a short time later. Reports surfaced that they had split after two years together. If they did actually break up, it was short-lived. By July 2022, they appeared to be back on. According to <a href=”https://www.eonline.com/news/1338503/kendall-jenner-and-devin-booker-are-fully-back-together-all-the-details-on-their-reconciliation”>E! News</a>, an insider claimed they had worked through a rough patch and decided to move on together.</p>
<p id=”par-4_76″>Moving on together was short-lived. By October 2022, they split yet again. Over the last two years, they’ve been <a href=”https://www.cheatsheet.com/news/devin-booker-spotted-with-kendall-jenner-again-how-many-times-have-they-broken-up-and-reconciled.html/”>spotted together off and on</a>. Still, they have refused to confirm or deny if they are seeing each other again. While rumors swirled earlier this fall that they had rekindled their romance, there is no concrete evidence to support those rumors. In total, the duo dated for about 2 years and 6 months before ending their relationship.</p>
<h2 class=”wp-block-heading” id=”h-her-romance-with-bad-bunny-went-viral-in-2023″>Her romance with Bad Bunny went viral in 2023</h2>
<p id=”par-5_78″>While Kendall Jenner and Devin Booker are prone to reuniting only to break up again, their romance when they are together is pretty low-key. The same can’t be said for Kendall’s relationship with Bad Bunny. The reality TV star and musician went very public with the relationship very quickly, and several interactions between the pair went viral. In fact, people are still talking about how Bad Bunny managed to make Kendall Jenner weak in the knees in public.</p>
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<p id=”par-6_51″>They first linked up in February 2023, when they were spotted leaving locations just minutes apart. They famously double-dated with Hailey and Justin Bieber during those early days. While they didn’t confirm the relationship right away, Bad Bunny appeared to throw shade at Devin Booker just a couple of months later.</p>
<p id=”par-7_88″>They largely confirmed the relationship in May 2023 and were spotted together throughout the summer and fall. Jenner and Bad Bunny stopped appearing together around November 2023, prompting fans to assume they had broken up. They confirmed their split in December 2023, and while <a href=”https://www.cheatsheet.com/news/kendall-jenner-bad-bunny-back-together-rumors-spark-met-gala.html/”>they briefly reconnected</a> the following year, it didn’t last. In total, Kendall Jenner and Bad Bunny dated for about a year; the romance didn’t last nearly as long as her relationship with Devin Booker. Still, it takes up plenty of room in fans’ minds.</p>