James Kennedy, the much-loved 34-year-old DJ and Vanderpump Rules star, is embracing a new chapter in parenthood. TMZ has reported that the reality TV star is expecting his first child with his new girlfriend, someone he has been with for around seven months. For someone who has already built a reputation for one of reality TV’s messiest dating histories, the news has come as a delightful surprise for his fans.
James Kennedy’s love life is significantly marked by high-profile romances and messy breakups, including a highly publicised engagement that was later called off and a domestic violence-related arrest.
Inside James Kennedy’s high-profile dating history
Before settling into a serious relationship with his new partner, Kennedy’s love life often played out publicly, thanks to his presence on reality television. The DJ first gained attention through his relationship with Kristen Doute on Vanderpump Rules. They became a much-loved pair of the show when they started dating in 2014, but the romance barely lasted a year. Their 2015 breakup was a messy one, as James ended up cheating on her with SUR employee Jenna Willis.
Pic: Bravo TV
Back then, Doute and Kennedy’s fallout drama became a major storyline of Vanderpump Rules, with explosive fights, Kristen’s insecurities about James, and his blatant lies. He eventually confessed to sleeping with Jenna and said:
“I feel bad about lying to Kristen, but, at the same time, I had good sex with Jenna. I don’t regret what happened with her. But I love Kristen, don’t get me wrong.”
Not long after his breakup with Doute, Kennedy began dating Rachel ‘Raquel’ Leviss in 2016 after meeting her at a New Year’s party. After a year of dating, they became Instagram official in 2017, and later, their relationship became one of the central arcs of the Bravo series. In May 2021, James proposed to Rachel in a grand ‘Rachella’-themed proposal, but by the end of that year, the engagement had been called off. They announced their split by stating:
“After these 5 wonderful years we had together, we decided we have two different goals and made the decision to call off the engagement. We love each other very much, but we aren’t in love anymore. We want nothing but the best for each other…”
Soon after the breakup, Kennedy started dating astrologer and podcast host Ally Lewber. The pair confirmed their relationship in early 2022 and later moved in together. Lewber eventually joined the cast of Vanderpump Rules, and their relationship unfolded publicly across multiple seasons.
What led to James Kennedy and Ally Lewber’s split? Inside the domestic violence allegations
Ally Lewber was another long-term relationship in James Kennedy’s life after Rachel Leviss. The couple dated for about three years and lived together in Burbank until their split in January 2025. During his time with Ally, James had expressed his desire to have children, start a family, and get married, but Ally was not so sure about that. Ally told in a May 2024 interview:
“I’ve known from the beginning, when I first met James, that he really did want a family, to have children, and to get married. And those are things that he really values.”
While James Kennedy’s past relationships often played out dramatically on reality TV, things reportedly escalated during Kathy Hilton’s Christmas party in 2024. A month later, Ally Lewber confirmed their breakup after police responded to an argument at the couple’s Los Angeles home. Kennedy was arrested on December 10, 2024, on a misdemeanor domestic violence charge and later released on a USD 20,000 bail, according to TMZ. Lewber was later identified as the woman involved in the incident.
After the breakup, Lewber stated that she was not physically hurt but admitted the relationship had reached a breaking point, especially amid Kennedy’s struggles with alcohol and sobriety. The DJ has since openly spoken about his struggles with alcohol.
Looking forward as a dad-to-be
For someone who has long desired a family life and become a father, fans are hoping that James Kennedy changes his erratic ways and builds a quieter and more stable life away from the chaos. Kennedy himself has not publicly addressed the pregnancy reports yet, nor has he revealed the identity of the mom-to-be.
It looks like James Kennedy is ready to settle down after a decade of chaotic romances. Congratulations to the parents-to-be.
Pic sources: James Kennedy/Instagram
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