Vanderpump Rules Alum James Kennedy’s Dating History

James Kennedy‘s love life has played out almost entirely on Vanderpump Rules — from drama-fueled hookup rumors in the early seasons to a five-year engagement, a whirlwind post-split romance and, most recently, a pregnancy announcement with a girlfriend fans barely knew existed.

After eight months of dating, Kennedy revealed in June 2026 that girlfriend Jordan Meyers is pregnant.

“We are thrilled to share that Jordan and I are expecting our first child together,” Kennedy told People. “We have previously kept our relationship out of the public eye, and this is the first time we’re sharing it publicly. We wanted to keep things personal while we were building our relationship together.”

Here’s a look back at every relationship that brought the DJ to this moment:

Kristen Doute

Before he settled down, Kennedy spent three seasons of Vanderpump Rules caught between costars Doute and Lala Kent. In April 2018, Doute defended her ex after an episode reignited claims the two had hooked up in Mexico, telling Us Weekly that Kennedy “did nothing wrong.”

“He was clearly intoxicated and not capable of anything at that moment,” Doute exclusively told Us of Kennedy’s conversation with Tom Sandoval and Jax Taylor. “It was actually really sad watching it back, because he had no idea what he was even saying and they took advantage of him.”

Taylor had claimed the pair hooked up in a hot tub outside his Mexico suite based on suspiciously positioned pillows — though Doute insisted she was never in the hot tub at all.

Rachel ‘Raquel’ Leviss 

Kennedy introduced Leviss as his serious girlfriend in 2016, and the pair dated for five years before calling off their engagement. Their romance survived multiple cheating allegations early on, including claims from a SUR employee that Kennedy had been unfaithful.

“Obviously, I understand all the rumors and drama and everything that’s happened on the show. You know we’ve basically gone through it together and I felt like these girls went to the end of the Earth to try and ruin my relationship,” Kennedy told Bravo in March 2017. “But we’ve stuck through everything and we love each other.”

The couple got engaged with a Coachella-themed proposal in May 2021, but two months after the proposal aired on Vanderpump Rules that October, Kennedy and Leviss announced they were splitting.

“After these 5 wonderful years we had together, we decided we have two different goals and made the decision to call off the engagement,” the exes wrote in identical Instagram statements in December 2021. “We love each other very much, but we aren’t in love anymore.”

Ally Lewber

Kennedy moved on quickly, meeting entertainment journalist Lewber in January 2022 — just three months after his split from Leviss. He went public on Kent’s “Give Them Lala” podcast the following month.

“I’m, kind of, seeing someone,” Kennedy said. “Look, it’s too early to say honestly [if Ally will appear on Vanderpump Rules]. I do like this girl, I really do.”

Lewber ultimately joined the VPR cast for seasons 10 and 11. When Bravo announced in November 2024 that the next season would feature a new lineup, Lewber told Us that Kennedy was “grieving and just feeling [his] emotions.”

The following month, Kennedy was arrested for misdemeanor domestic violence — charges his legal team denied and that were subsequently dropped.

“I am taking time to focus on my sobriety, personal growth, and being present for my loved ones,” he wrote via Instagram in December 2024.

Lewber confirmed their split in January 2025.

Jordan Meyers

Kennedy went public with the social media influencer while announcing their pregnancy in June 2026.

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“I’m from North Carolina, so I went to visit James for what was supposed to be ‘three days,’ which has now turned into eight months together,” Meyers told People. “The second I met James, we instantly felt such a strong spark between us.”

Kennedy added, “As we get ready to welcome our baby, we’re focused on embracing all of the joy, growth and change that comes with becoming parents.”

This story was compiled with the help of AI tools and edited by journalists.