If you have been watching Perfect Match season 4 and wondering about the ex Ally Lewber keeps mentioning, you are not alone. Ally, an astrologer by trade, first gained attention on Vanderpump Rules as the girlfriend of DJ James Kennedy. Their relationship lasted roughly three years, included public vacations and a musical collaboration, and ended after a serious incident in late 2024. Now, Ally is navigating a very different kind of romance on a reality dating show.
The Beginning: How Ally Lewber and James Kennedy Met
James Kennedy ended his engagement to Rachel Leviss in December 2021. That breakup made headlines among Vanderpump Rules fans, as the couple had been together for several years. Just about six weeks later, James began dating Ally Lewber. The pair confirmed their relationship during part two of the Vanderpump Rules season 10 reunion.
During that reunion, James addressed the timing of his new romance. “I think everyone does process breakups differently. For me, it was enough time,” he said. Ally added her own perspective: “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.”
For many viewers, the speed of this transition raised eyebrows. Moving from a broken engagement to a new relationship in roughly six weeks is fast by any standard. Yet both parties insisted they had communicated openly about their intentions from the start.
February 2022: First Hints of a Public Romance
In February 2022, James appeared on Vanderpump Rules co-star Lala Kent’s podcast, Give Them Lala. When asked whether fans might see Ally on the next season of the show, James was cautious. “Look, it’s too early to say, honestly. I do like this girl, I really do,” he shared, according to Page Six. He added, “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.”
This statement reveals something important about the early stages of their relationship: James was aware that bringing a new girlfriend onto a reality show is a major decision. It is not just about personal comfort — it also invites public scrutiny. By giving Ally space to choose, he showed a degree of consideration that some fans may not have expected.
March 2022: Public Appearances and a Tulum Vacation
By March 2022, the couple was ready to be seen together in a more deliberate way. They traveled to Tulum, Mexico, for a vacation that James described as transformative. “Only the most magical trip I’ve ever experienced in my entire life, here’s a little slide show of today’s adventure,” he wrote on Instagram. He also posted a message urging followers to “share the love people! and the positivity! cause life’s too short.”
That same month, James and Ally attended the iHeartRadio Music Awards together. Walking a red carpet as a couple for the first time signals a certain level of seriousness. For reality TV personalities, these public appearances serve as a way to introduce a partner to a wider audience. It also gives media outlets a reason to write about the new pairing, which can strengthen a couple’s public image.
April 2022: Jamaica and Coachella
The couple kept traveling throughout spring 2022. They took a trip to Jamaica, sharing sunny photos that made fans envious. Shortly after, they attended the Coachella Valley Music and Arts Festival together for the first time. James posted a selfie of the two cuddled up, captioning it, “This is my favorite pic from night 1.”
Attending a major music festival as a couple is a milestone for many relationships. It involves navigating large crowds, coordinating schedules, and spending extended time together in a high-energy environment. For James, a DJ who performs at such events, having Ally there likely felt natural. For Ally, it meant stepping into a world of loud music, late nights, and constant attention from fans and photographers.
July 2022: Going the Distance
By July 2022, James felt confident enough to speak openly about his future with Ally. In an interview with Us Weekly, he said, “We’re really, truly best friends and I really do see it going the distance.” He also explained his approach to relationships: “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.”
This quote is interesting because it shows James’s self-awareness about his own romantic patterns. He acknowledges that he moves quickly when he feels a strong connection, but he also insists he is not reckless. For Ally, hearing these words in public must have been reassuring. It suggested that James saw her as more than a rebound.
November 2022: Another Vacation
The couple continued their pattern of frequent travel in November 2022. They went on yet another vacation, though specific details about the destination were kept somewhat private. For a couple in the public eye, these trips serve multiple purposes. They create content for social media, strengthen the bond between partners, and offer a break from the pressures of filming reality television.
By this point, Ally and James had been together for about ten months. They had traveled to multiple countries, attended major events, and spoken publicly about their feelings. To outside observers, they seemed stable and happy.
January 2023: Ally’s Birthday in New York City
In January 2023, the couple celebrated Ally’s birthday in New York City. They posted photos that showed them smiling, dressed up, and clearly enjoying each other’s company. New York in winter has a romantic quality — the holiday lights, the cold air, the cozy restaurants. For Ally, having James plan a birthday trip to such a iconic city likely felt special.
Celebrating a partner’s birthday in a meaningful way is often a sign of investment in the relationship. It shows that one person is willing to put time, money, and thought into making the other person feel valued. In the context of their relationship, this birthday trip suggested that James was fully committed.
February 2023: Ally Opens Up About Love
In February 2023, Ally gave her own interview to Us Weekly. She described James as the more romantic partner. “He’s the romantic one. It’s harder for me to say ‘I love you,'” she admitted. “He wears his heart on his sleeve more than I do, but I do [love him]. He knows that.”
This interview is revealing because it shows a dynamic that many couples experience: one partner is more openly expressive, while the other is more reserved. For Ally, saying “I love you” may have felt vulnerable, especially with cameras and microphones nearby. Yet she made a point to say that James knew how she felt. That kind of private assurance can be more important than public declarations.
Ally Joins Vanderpump Rules
Also in February 2023, Ally began making frequent appearances on Vanderpump Rules. During one of James’s confessionals, he shared more details about their origin story. “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,” he said. He added, “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.”
This confessional was raw and unfiltered, which is typical for James. It also highlighted the tension that surrounded their relationship from the beginning: the speed of the transition. By appearing on the show, Ally was essentially stepping into the middle of a story that viewers had been following for years. She had to prove herself not just to James, but to an audience that was still processing his breakup with Rachel.
May 2023: An Appreciation Post
In May 2023, James posted an appreciation post for Ally on Instagram. “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,” he wrote. The post included photos of Ally looking happy and confident.
Public appreciation posts can serve as a relationship milestone. They signal to the world that one partner is proud of the other. For Ally, who was still building her public profile, having James’s endorsement likely helped her gain acceptance among Vanderpump Rules fans.
You may also enjoy reading: Clues Jimmy Presnell & Ally Lewber Still Together.
August 2023: The Eras Tour
In August 2023, the couple attended Taylor Swift’s Eras Tour together. They posted photos from the concert, looking thrilled to be there. Attending a massive tour like the Eras Tour is a shared experience that can bring couples closer. The music, the crowd, the energy — it creates lasting memories.
For many couples, attending a concert together is a test of compatibility. Do you like the same music? Can you handle the crowd? Do you have fun together in a high-stimulation environment? For James and Ally, the answer seemed to be yes.
November 2023: BravoCon
In November 2023, James and Ally attended BravoCon together. This is the annual fan convention for the Bravo network, where reality stars from various shows gather to meet fans and participate in panels. For Ally, attending BravoCon as James’s girlfriend was a big step. It meant being fully integrated into the Bravo universe, not just as a guest on Vanderpump Rules but as a recognized figure in her own right.
The couple looked polished and happy at the event. They posed for photos, interacted with fans, and seemed comfortable in the spotlight. For many observers, this appearance solidified their status as a serious couple.
December 2023: A Musical Collaboration
In December 2023, James and Ally released their first single together, “I Believe in You.” The song was a collaboration with Station Littl, and it marked a new chapter in their relationship. Creating music together is an intimate act. It requires trust, creativity, and a willingness to be vulnerable. For a couple to write and record a song, they must be in sync emotionally and artistically.
The release of the single suggested that James and Ally were building a life together that went beyond reality television. They were creating something original, something that belonged to both of them. For fans, the song was a sweet declaration of love and commitment.
December 2024: The Arrest and the Breakup
In December 2024, James Kennedy was arrested on suspicion of domestic violence. This event marked a dramatic turning point in the relationship. Shortly after the arrest, Ally and James ended their three-year relationship. The breakup was not a quiet, private affair — it became public knowledge almost immediately, given James’s status as a reality star.
For Ally, the end of the relationship was clearly painful. In interviews ahead of the Perfect Match premiere, she described the split as “heavy.” She told Tudum that her friend Rachel Recchia, who participated in Perfect Match season 3, encouraged her to join the show. “I was really, really hesitant at first,” Ally said. “My friend Rachel 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.”
This quote reveals a lot about Ally’s mindset after the breakup. She was hesitant but willing to try something new. She recognized that her pattern of jumping into serious relationships had not served her well. By joining Perfect Match, she was deliberately stepping outside her comfort zone.
What the Relationship Taught Ally
Looking back at the full timeline, it is clear that Ally and James had a relationship that moved quickly, burned brightly, and ended under difficult circumstances. They traveled the world, made music together, and faced public scrutiny as a couple. They also dealt with serious issues, including James’s arrest.
For Ally, the experience seems to have been a learning opportunity. In her interviews, she emphasizes the importance of taking things slow and being open to new experiences. She does not dwell on the negative aspects of the breakup. Instead, she focuses on her own growth.
This is a valuable lesson for anyone who has been through a difficult breakup. It is easy to get stuck in a cycle of blame or regret. But Ally’s approach — acknowledging the pain, then moving forward — is a healthier path. She does not pretend the relationship was perfect, but she also does not let it define her.
What Comes Next for Ally Lewber
As of now, Ally is appearing on Perfect Match season 4, where she is balancing romances with Jimmy Presnell, Hashim Moore, and Dave Hand. The show is a dramatic departure from her previous relationship. Instead of one serious partner, she is exploring multiple connections in a controlled, televised environment.
It remains to be seen whether Ally will find lasting love on Perfect Match. But regardless of the outcome, her decision to participate shows resilience. She is not hiding from the public eye after her breakup. She is stepping into a new challenge, one that requires her to be vulnerable, open, and willing to take risks.
For fans who have followed her journey from Vanderpump Rules to Perfect Match, Ally’s story is a reminder that relationships — even painful ones — can lead to personal growth. The three years she spent with James Kennedy were intense, public, and ultimately ended in heartbreak. But they also gave her the confidence to try something new, to trust herself, and to believe that love is still possible.
