The Evolution of James Kennedy’s Love Life
For years, James Kennedy’s personal life has been a cornerstone of Vanderpump Rules. Viewers have watched him navigate everything from early-season relationship rumors and a long-term engagement to high-profile breakups and the recent surprise news that he is expecting his first child.
The News of a New Chapter
In June 2026, Kennedy shared a major life update: he and his girlfriend, Jordan Meyers, are expecting a baby. The couple, who have been together for eight months, previously chose to keep their romance out of the public spotlight.
“We are thrilled that Jordan and I are expecting our first child together,” Kennedy shared in an interview. “We wanted to keep things personal while we were building our relationship together.” Meyers added, “The second I met James, we instantly felt such a strong spark between us.”
Early Scandals and Kristen Doute
Before his more serious relationships, Kennedy’s time on the show was marked by a turbulent dynamic involving costar Kristen Doute. In 2018, allegations surfaced regarding an intimate encounter between the two in Mexico. Doute publicly defended Kennedy, claiming he was not in a state to be held responsible for the events in question.
“It was actually really sad watching it back, because he had no idea what he was even saying and they took advantage of him,” Doute noted at the time, refuting claims made by fellow cast members regarding the nature of their interaction.
The Engagement to Rachel ‘Raquel’ Leviss
Kennedy and Rachel Leviss began dating in 2016. Their five-year relationship faced constant scrutiny, including various allegations of infidelity that plagued the couple early on. Despite the drama, they remained together and eventually got engaged during a Coachella-inspired proposal in May 2021.
However, the engagement was short-lived. Just months later, in December 2021, the pair announced their separation. “After these 5 wonderful years we had together, we decided we have two different goals and made the decision to call off the engagement,” they stated. “We love each other very much, but we aren’t in love anymore.”
The Relationship with Ally Lewber
In early 2022, Kennedy began dating entertainment journalist Ally Lewber. The relationship moved quickly, and Lewber soon became a fixture on Vanderpump Rules for seasons 10 and 11. The couple eventually parted ways in January 2025, following a difficult period for Kennedy that included legal challenges, which were later dismissed, and a renewed focus on his sobriety and personal growth.
Moving Forward with Jordan Meyers
Following his split from Lewber, Kennedy found stability with Meyers. As they prepare to welcome their child, Kennedy emphasized his current mindset: “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.”