<p>From reality stars linking up with pop icons to age-gap romances no one saw coming, these surprising celebrity pairings prove that love in Hollywood doesn&rsquo;t always follow a script.</p>

<p data-start="115" data-end="335">In the world of celebrity, it&rsquo;s common to see the hottest actors or musicians link up and become an <a href="https://www.lofficielusa.com/pop-culture/forgotten-celebrity-couples-2000s-y2k" target="_blank" rel="noopener">It couple</a>&mdash;whether it lasts a moment, a marriage, or a lifetime. And from the outside looking in, it usually makes sense.</p>
<p data-start="337" data-end="694">Of course Ashton Kutcher and Mila Kunis ended up together&mdash;they starred on <em data-start="411" data-end="427">That '70s Show</em> for years and just <em data-start="447" data-end="453">look</em> good together. And <a href="https://www.lofficielusa.com/fashion/beyonce-jay-z-louis-vuitton-mens-spring-summer-2026-show" target="_blank" rel="noopener">Beyonc&eacute; and Jay-Z?</a> Two of the most influential figures in music, and they&rsquo;ve built an empire side by side. But every so often, pop culture fanatics are thrown for a loop when a truly unexpected pairing hits the headlines.</p>
<p data-start="696" data-end="974">Take Pete Davidson and Kim Kardashian&rsquo;s <a href="https://www.lofficielusa.com/pop-culture/kim-kardashian-pete-davidson-officially-dating" target="_blank" rel="noopener">relationship</a> in 2021&mdash;it practically broke the internet. The latest eyebrow-raising couple? 49-year-old singer Sia and <em data-start="854" data-end="873">Too Hot to Handle</em>&rsquo;s 28-year-old Harry Jowsey, who were spotted holding hands this past weekend. How did <em data-start="960" data-end="966">that</em> happen?</p>
<p data-start="976" data-end="1256">Naturally, the internet&rsquo;s deep dive has resurfaced a handful of other celebrity pairings that feel so random, it&rsquo;s as if they were generated by a Hollywood name-pairing bot. Zach Braff and Florence Pugh? A head-scratcher. Lena Dunham and <a href="https://www.lofficielusa.com/pop-culture/jack-antonoff-dating-history-margaret-qualley-lena-dunham-lorde" target="_blank" rel="noopener">Jack Antonoff</a>? Didn&rsquo;t see that one coming.</p>
<p data-start="1258" data-end="1444"><em>L&rsquo;OFFICIEL</em> rounds up more of these unexpected <a href="https://www.lofficielusa.com/pop-culture/5-surprising-celebrity-couples" target="_blank" rel="noopener">celebrity couples</a>&mdash;past and present. Most of them didn&rsquo;t last (shocking), but their pairings live on in the archives of pop culture oddities.</p>

harry jowsey and sia dating age gap

<h2>Kylie Jenner and Timoth&eacute;e Chalamet (2023-Present)</h2>

timothee and kylie dating

<h2>Selena Gomez and Benny Blanco (2023-Present)</h2>

unexpected celebrity couples, selena gomez benny blanco

<h2>Lena Dunham and Jack Antonoff (2012-2017)</h2>

lena dunham and jack antonoff dating history

<h2>Jojo Siwa and Chris Hughes (2025)</h2>

<h2>Zach Braff and Florence Pugh (2019-2022)</h2>

weird celebrity couple pairings

<h2><span>Madelaine</span> Petsch and Tyga (2025)</h2>

weird celebrity couples

<h2>Tiger Woods and Vanessa Trump (2025)</h2>

<h2>Matthew McConaughey and Janet Jackson (2002)</h2>

<h2>Miley Cyrus and Patrick Schwarzenegger (2014-2015)</h2>

<h2>Brenda Song and Trace Cyrus (2010-2017)</h2>

, weird celebrity couples

<h2>Kim Kardashian and Pete Davidson (2021-2022)</h2>

Hollywood’s Most Unexpected Celebrity Couples

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