'Vanderpump Rules' Alum James Kennedy's Dating History Through the Years
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
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 went public with the social media influencer while announcing their pregnancy in June 2026.
"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.
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This story was originally published June 12, 2026 at 2:50 PM.