James Kennedy & Jordan Meyers: Engaged! Third Time’s the Charm?
<div><img width="300" height="169" src="https://cdn.thehollywoodgossip.com/uploads/2026/07/0701_jameskennedy_jordanmeyers_header-300x169.jpg" class="attachment-medium size-medium wp-post-image" alt="James Kennedy and his pregnant, much younger girlfriend (now fiancee) Jordan Meyers in June 2026." style="margin-bottom: 15px;" decoding="async" loading="lazy" srcset="https://cdn.thehollywoodgossip.com/uploads/2026/07/0701_jameskennedy_jordanmeyers_header-300x169.jpg 300w, https://cdn.thehollywoodgossip.com/uploads/2026/07/0701_jameskennedy_jordanmeyers_header-1024x576.jpg 1024w, https://cdn.thehollywoodgossip.com/uploads/2026/07/0701_jameskennedy_jordanmeyers_header-768x432.jpg 768w, https://cdn.thehollywoodgossip.com/uploads/2026/07/0701_jameskennedy_jordanmeyers_header-2048x1152.jpg 2048w, https://cdn.thehollywoodgossip.com/uploads/2026/07/0701_jameskennedy_jordanmeyers_header-728x410.jpg 728w, https://cdn.thehollywoodgossip.com/uploads/2026/07/0701_jameskennedy_jordanmeyers_header-960x540.jpg 960w, https://cdn.thehollywoodgossip.com/uploads/2026/07/0701_jameskennedy_jordanmeyers_header-1080x608.jpg 1080w, https://cdn.thehollywoodgossip.com/uploads/2026/07/0701_jameskennedy_jordanmeyers_header-1200x675.jpg 1200w" sizes="auto, (max-width: 760px) calc(100vw - 20px), 720px" /></div> <p><span class="span-reading-time rt-reading-time" style="display: block;"><span class="rt-label rt-prefix">Reading Time: </span> <span class="rt-time"> 2</span> <span class="rt-label rt-postfix">minutes</span></span>It's been only months since they began dating, and only weeks since they shared the pregnancy news.</p> <p><a href="https://www.thehollywoodgossip.com/2026/07/james-kennedy-engaged-jordan-meyers-pump-rules/">James Kennedy & Jordan Meyers: Engaged! Third Time’s the Charm?</a> was originally published on <a href="https://www.thehollywoodgossip.com">The Hollywood Gossip</a>.</p>
By Author Simon Delott
Published: Jul 01, 2026 at 10:32 AM • Category General Celebrity News
Reading Time: 2 minutes
If at first you don’t succeed …
Vanderpump Rules villain James Kennedy is now engaged.
He proposed to Jordan Meyers, his 23-year-old girlfriend . She said yes.
And folks on the internet who are familiar with his track record are, at best, rolling their eyes.
On Tuesday, June 30, Kennedy took to his Instagram page to share the news.
He shared a photo of what must have felt like a romantic proposal at Villa d’Este on Lake Como in Italy.
(If you didn’t recognize the famous backdrop, he geotagged the pic for your convenience.)
Kennedy shared snaps of him going down on one knee to propose to Meyers, who is both pregnant and not yet old enough to rent a car.
He wore a white shirt with a plunging neckline, while Meyers wore a beautiful red dress.
A post shared by James Kennedy (@itsjameskennedy)
For his caption, Kennedy — who should really be more practiced at this by now — left one of the most broad-brush and impersonal captions imaginable.
“We’re engaged!!” he began.
“I love you,” Kennedy gushed, “adventures with you forever and ever.”
He then wrote: “Thank you for making me the luckiest guy in the world.”
Kennedy punctuated this deeply bland caption with a red heart emoji and with a fire emoji. Okay.
Truth be told, this engagement is not a huge surprise.
Is it a good idea? No. But is it surprising? Not really, given the context.
Yes, Meyers is frankly too young to get married. And yes, they’ve only been dating for a matter of months.
However, Meyers is pregnant . Whoops!
If you’re seeing red flags here, well, you’re not alone.
Kennedy was engaged to Raquel Leviss back in the day. The erstwhile couple split in 2021.
He would later move on with Ally Lewber, as documented on Vanderpump Rules .
Notably, their breakup included harrowing allegations of physical abuse .
This scandal was so bad that Kennedy even earned condemnation from Lisa Vanderpump , despite her track record of sort of handwaving most bad behavior from men.
Hopefully, Meyers will make the right choice. No one should be tethered to this dude for long.