A Complete Timeline Of James Kennedy’s Relationships

James Kennedy got his start in the public eye after appearing on Season 2 of Vanderpump Rules. The Bravo star had an interesting background, as his godfather was legendary singer George Michael and he was dating fellow castmate Kristen Doute at the time of filming. His introduction made him a unique member of the series.

Today, James is a household name with and without the iconic Bravo reality TV show. However, his road to fame hasn’t always been smooth, especially with public romances with fellow Vanderpump Rules costars.

Sadly, in December 2024, TMZ reported that James was arrested for domestic violence while dating co-star, Ally Lewber. While the story is developing, a deep dive into his past relationships could show snippets of similar aggressive behaviors or speed bumps with former partners.

James Kennedy's Relationship Timelines

In Season 2 of Vanderpump Rules, a young James Kennedy started appearing on the series as a fellow worker at SUR. As viewers saw the demise of Tom Sandoval and Kristen Doute's relationship, they saw the beginning of her bond with James.

Kristen Doute

Kristen Doute and James Kennedy dated between 2014 and 2015, according to People. The couple appeared smitten with one another while Vanderpump Rules cameras were filming, but the toxicity in their relationship eventually became apparent.

• Kristen started dating James right after her breakup with Tom Sandoval — a move many felt was made to make Tom jealous.

While happy at first, the two started fighting and had a rollercoaster relationship. In an interview with The Daily Dish, Kristen shared that she felt "used" by James to get on the show. "James did his homework. He knew exactly what to do to get me." She continued, "He knew when to swoop in — when I wasn’t really friends with anyone yet. [He also knew] basically don’t act like Tom [Sandoval] and don’t be an a**, and then I’m going to like him."

According to Page Six, Kristen also said that James was physically abusive during their time together. Fans will remember the pair drunkenly fighting at Scheana Shay's wedding, where Kristen slapped James across the face during an argument.

Lala Kent

Although Lala Kent and James Kennedy never officially dated while filming Vanderpump Rules, the two had a very public "situationship" that took over the fandom.

Lala joined the series in Season 4 as a new hostess at SUR. She and James quickly became flirty with one another. While Lala wanted to keep her options open as the new girl at SUR, James was adamant about being with Lala. Lala explained James was a guy she "made out" with and with whom she made music, as reported by Bravo.

By the end of Season 4, Lala and James had more defined rules to their relationship. "We're friends that make out, and you can have anybody touch your peep, [but] you can never get mad if anything happens, because I've laid it out," she explained. And while she said they weren't sleeping together, she eventually admitted to hooking up for the first time after Katie Maloney and Tom Schwartz got engaged.

I don't regret sleeping with James.

The two eventually realized they were better off as friends without intimacy, but in Season 10, Lala shocked fans when she said that she and James slept together when he first started dating Rachel (formerly known as Raquel) Leviss and she was with Randall Emmett.

Bravo mentioned the hookup happened in 2016 after one too many cocktails. James said on an episode of Vanderpump Rules, “A lot of guys make mistakes, OK? Obviously, half of Lala wanted it to happen too, right? So let’s not dilly dally."

Despite the previous flirtation, the two have remained close friends and are still close.

Rachel Leviss

Rachel Leviss and James Kennedy had one of the more notable relationships while on Vanderpump Rules. US Weekly reported that the two met at a New Year's party in 2016 and started dating shortly after.

Fans were suspicious of Rachel because it was rumored that she was a fan of the series before meeting James and that her intentions with the DJ weren't authentic. James ignored the commentary and continued dating Rachel.

In Season 5, multiple women who worked at SUR approached Rachel, telling her they had recently slept with James and that he wasn't faithful to her while she was in college. Rachel didn't believe the women's allegations and stayed by James' side.

• By 2018, the pair were more serious and moved in with each other, giving Rachel more space on Vanderpump Rules.
• In 2019, James told US Weekly about his hopeful plans for the future with Rachel. “Me and Raquel are super great. We're super happy together. She’s the love of my life. I love her.”
• By 2021, the duo were engaged. Vanderpump Rules viewers saw James' collaboration with the rest of the cast as he proposed to Rachel.

By the end of Season 9, James and Rachel shocked fans by calling off their engagement. While filming, Rachel explained her family didn't love James, and she always felt in the middle between her fiancé and her family. Ultimately, the pandemic took a toll on their relationship and, according to Page Six, the couple weren't intimate for two years.

A year after breaking up, James was horrified to find out that Rachel had an affair with their cast mate and close friend, Tom Sandoval. Now known as "Scandoval," the scandal took over the reality TV universe and became one of the biggest Bravo scandals because no one had any inclination that the two were sleeping together while Tom was also with his girlfriend of ten years, Ariana Madix.

James' journey to sobriety began when Rachel gave him an ultimatum. He struggled with alcoholism and the erratic behaviors that followed for years until he decided to better himself.

Ally Lewber

Ally Lewber and James Kennedy appeared to be end game. According to Cosmopolitan, James and Ally started dating a little over a month after he and Rachel ended their five-year relationship. Fans were taken aback by how quickly he moved on — many assumed Ally was another rebound. “I think everyone does process breakups differently. For me, it was enough time,” James shared on Vanderpump Rules.

In 2022, James shared on the Give Them Lala podcast that he was taking things slow with Ally and had no expectations for their relationship or what she wanted to be shown on camera. Later that summer, however, the two became more serious.

“I’ve always been true to myself. So if I didn’t see anything going anywhere, I really wouldn’t jump into something quickly. But I don’t really put a timer on anything in life. Like age, time is all relative. So it doesn’t really matter," James told US Weekly.

By 2023, the pair were more serious and Ally made more appearances on Vanderpump Rules​​​​​​, infiltrating her way into the group seamlessly. As seen in the series, James bought this first home, Ally moved in, and they raised their dog and cat together in their new, cozy life.

Ally told Variety in 2024, “I wish people could see more of us, because our relationship off-camera is a lot more funny, silly, and creative. We really push each other. He’s my biggest cheerleader, and I’m his. And so I think that’s the only thing that hurts is when I see comments questioning my love for him, because I do love him."

Unfortunately, in December 2024, TMZ reported that James was arrested for a domestic violence incident and released on a $20,000 bond. As of this article's publishing, Ally's name isn't in the police report, but to be classified as a domestic violence incident, it involved a partner in his home.

Officially, James was arrested for misdemeanor domestic violence, with charges still pending.

Not much is known about the incident thus far, but Deadline reported that James and Ally were at Kathy Hilton's holiday party before the police were called. Sources alleged James acted "erratic" and was seen yelling at Ally at the party.

James' arrest is a developing story. The two haven't released a statement as of this article's publishing.