Hello to everyone who’s been watching Perfect Match season 4 and thinking, “Um, who is this ex that Ally Lewber keeps referring to?” Though she’s been balancing romances with Jimmy Presnell and Hashim Moore (and Dave Hand…) on Perfect Match, the astrologer is best known for her time on Vanderpump Rules and her three-year relationship with VPR alum James Kennedy.
Ahead of the Perfect Match premiere, Ally opened up to Tudum about her tumultuous romance with James, saying how their “heavy” split led her to the dating show. “I was really, really hesitant at first,” she said. “My friend Rachel [Recchia] participated in season 3, and she was like, ‘Do it. Trust me, Ally, I know you’re going to have so much fun.’ I’ve always been in serious relationships, and I’ve never really done the dating apps or traditional going on dates. I was like, ‘That sounds fun and terrifying.’ They say fear is a good thing, so I leaned toward it.”
As a reminder, Ally and James met shortly after he decided to call it quits with Rachel Leviss, and while they seemed to be going strong for years, things took a turn after James was arrested on suspicion of domestic violence in December 2024. Need a quick review on their ’ship? Here’s a comprehensive timeline of their relationship, from the very beginning to their eventual breakup.
January 2022
Ally and James began dating roughly six weeks after the DJ ended his engagement to Rachel Leviss in December 2021, which they later confirmed during part two of the Vanderpump Rules season 10 reunion.
“I think everyone does process breakups differently. For me, it was enough time,” James revealed before Ally jumped in and noted, “We definitely both went into it planning to take things slow. I mean, we did jump into it, but a lot of conversations were had about it.”
February 2022
While appearing on Vanderpump Rules costar Lala Kent’s podcast Give Them Lala, James was asked whether fans can expect to see Ally on the next season of the hit show.
“Look, it’s too early to say, honestly. I do like this girl, I really do,” he dished (per Page Six) before adding, “I don’t know. We’ll see what happens. I can’t ask any girl to do that. With [Ally], I’m taking my time. She gets to really choose what she wants to do with that whole situation, and then for me, it’s like, I have to decide as well.”
March 2022
“Only the most magical trip I’ve ever experienced in my entire life, here’s a little slide show of todays adventure,” the reality star penned on Instagram alongside snaps from his and Ally’s Tulum, Mexico, vacation. “Share the love people! and the positivity! cause life’s too short 😉🌊✨🌙.”
That month, the two continued to take their romance public with an appearance at the iHeartRadio Music Awards.
April 2022
The duo made a buncha memories together, from a trip to Jamaica...
...to spending their first Coachella together. “This is my favorite pic from night 1,” James captioned a cute selfie of himself and his girlfriend cuddled up at the music festival.
July 2022
“We’re really, truly best friends and I really do see it going the distance,” the DJ confessed to Us Weekly about his ’ship. “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 time on anything in life. Like age, time is all relative. So it doesn’t really matter.”
November 2022
Another month, another vacay for these two!
January 2023
The couple celebrated Ally’s b-day in NYC and looked so in love. ❤️
February 2023
It was Ally’s turn to gush about her and James’s love story. “He’s the romantic one. It’s harder for me to say [I love you],” she dished to Us Weekly. “He wears his heart on his sleeve more than I do, but I do [love him]. He knows that.”
That same month, Ally began making frequent appearances on Vanderpump Rules, and fans found out more details about their ~origin story~ during one of James’s confessionals.
“I met Ally about five or six weeks after Raquel and I broke up. A lot of people would say that’s really soon, but you can’t put a fucking date on love,” the DJ explained during the season 10 premiere of the hit show. “I’m not even that guy that would just get a girlfriend for the fuck of it. Unless I’m fucking obsessed and I need that ass in my bed every time I wake up.”
May 2023
“This is an Ally Bally appreciation post! I’m super proud of her and everything she’s doing! she truly is my bestie. Love you❤️🔥,” James gushed alongside a buncha loved-up snaps of them.
August 2023
The couple made us all types of jealous by stepping out at the Eras Tour together.
November 2023
James and Ally joined the rest of the Vanderpump Rules cast at BravoCon and looked *chef’s kiss*.
December 2023
The duo teamed up for their first single, “I Believe in You,” and opened up about the project during a convo with Us Weekly. “It’s been an incredible experience collabing with Station Little on this,” James said of the track. “Ally and I have been working on a lot of music this year, and this is just a great way to add to the collection that we’re going to be releasing soon.”
“This song is all about following your dreams, which is a message that I’m very passionate about,” Ally added. “I’m from Ohio and moved to L.A. with some big dreams, and I know [James] agrees and had some big dreams as well.”
February 2024
Ally spilled all the deets on her and James’s Valentine’s Day plans to BravoTV.com, saying, “Oh my gosh, I think that James has a show in New York City, which is my favorite city.”
“I’m pretty sure he is going to have a show, but then we’ll do a Broadway show because that’s what we did last year, and it’s our favorite thing to do together now; I got him into theater and Broadway,” she added.
April 2024
Ally opened up to Variety about her experience being on the show and all the reactions she’s gotten from the public. “I’m super grateful and lucky, because I do feel like the majority of [fan’s comments on social media] are really nice. And the ones that aren’t, I have gotten really good at not paying attention or not letting them get to me,” she said before noting, “I think that the ones that get to me are the ones that question my love for James and my intentions. That is always hard to read, because it’s not up to anyone else to decide. They see literally 30 minutes, not even, probably five minutes of me on TV. He’s such a lovely person. He has Venus in the first house—I always use that to explain it to people. And my Venus is in the 12th house, so I am pretty private.”
“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,” she added.
May 2024
Fans got up to speed on where the couple is at re: their future. “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,” Ally explained to The Daily Dish. “I feel differently, but I do see myself having kids one day. But I feel like we’re both just so busy and I’m just so happy with where we’re at.”
She added, “I’m more of a slow person. I take it day by day where, you know, James is very quick with it. I’m, like, we have forever. We have all the time in the world. And I just want us to enjoy this chapter where we’re at now ’cause we’re so happy.”
She concluded with, “I’m just not there yet in life and James does know that, and so we’ve talked about it and he knows and he’s happy to wait as long as he will. [But] he shouldn’t wait forever because I know that is something that’s really important to him.”
June 2024
Ally posted this cute carousel of her May moments with James and we’re 🥺❤️:
December 2024
On December 10, James was arrested on suspicion of domestic violence after the police were called "regarding an argument between a man and a woman," as a police spokesperson confirmed to People at the time.
At the time, TMZ (citing a law enforcement source) reported that a witness reportedly saw the DJ get physical with the unnamed woman, though authorities did not see any injuries when they arrived on the scene. He was eventually released on bail.
A few days later, another source for TMZ claimed Ally would be sticking up for James, and the two weren't planning on breaking up over the arrest.
January 2025
Just about a month after James's arrest on January 22, Ally took to Instagram to confirm she and James had gone their separate ways. "Thank you for all your support and kindness," she wrote in a statement posted to her Instagram Stories. "I am happy that prosecutors decided not to file against James as I never desired criminal charges. We had an argument outside of his home related to him drinking again, however, I was not physically hurt."
She admitted that she was “shocked by the headlines and disheartened by how the event was portrayed” but that she and James were, indeed, done. “We are no longer together, but I'll always support James and wish him the best with his sobriety and healing. Thank you for your understanding,” she ended her message.
April 2025
During an interview with People, Ally opened up about the breakup and how her ex’s arrest served as a “wake-up call” for her. “I never was physically hurt and I never felt unsafe,” she said. “I think it was more just walking on eggshells and feeling anxious about, when is his next blow-up going to be?”
She added, “And I didn’t even realize this really until I was out of the house for a while, but just how my nervous system just feels normal again. It was always kind of anxious of making sure that he doesn’t get upset. Monitoring someone’s behavior is not healthy.”
May 2026
TMZ broke the news that James is expecting a baby with his new girlfriend (who hasn’t been publicly named)…but thankfully, Ally didn’t seem bothered by the bombshell. As she explained during an appearance on the Scheananigans with Scheana Shay podcast, she was actually “shocked” how little she cared about the news.
“I didn’t know he, like, had a girlfriend,” she explained of seeing that video of James with a mysterious blonde at Coachella in April. She added that she wished him “the best,” noting, “He has always wanted to be a dad. That was always our thing—he always wanted kids immediately, and I was like, ‘I don’t know what I want.’”
No bad blood here, it seems!
