Red Flags In Matt James & Rachael Kirkconnell's Relationship

When Matt James was cast as the lead of "The Bachelor," fans were stoked. Not only was he the first Black man to take that role, but he was also part of the famously charismatic "Quarantine Crew" on TikTok. As the show finally began to unfold, it seemed more and more likely that James would find love on TV. After all, the contestants on Matt James' season were enthusiastic about his personality. Plus, he had developed particularly good chemistry with Georgia-based graphic designer Rachael Kirkconnell — to the delight of social media users everywhere.

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Even as viewers watched James and Kirkconnell fall in love on the small screen, though, all was not well. To the shock and horror of many, red flags began to emerge in the couple's fledgling relationship. While the season was still airing, internet sleuths uncovered some inappropriate photographs from Kirkconnell's past — including a number of racially insensitive shots. This discovery called into question everything from Kirkconnell's character to her feelings for James. Because of the resulting scandal, the newly minted couple was drawn into a massive public debate that involved a messy breakup, a confusing separation, and a romantic attraction that was constantly strained by the pressures of their newfound celebrity. Since then, things have not gotten easier for the couple. If anything, more issues have emerged in their relationship.

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Rachael Kirkconnell was involved in a racism scandal

At first, Rachael Kirkconnell's relationship with Matt James looked like something out of a fairy tale. Sure, it might have been a little strange that the pair fell in love on national TV, but at the same time, the "Bachelor" franchise seemed to set the couple up for success, fostering an environment that allowed the couple's feelings to progress so quickly that they began falling in love after just five weeks of dating.

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Nevertheless, the romance between Kirkconnell and James imploded before their season had even finished airing. The trouble began when fans of the show uncovered photographs of Kirkconnell at a 2018 "Old South" party held by the Robert E. Lee-inspired fraternity, Kappa Alpha Order. According to the pictures, which were later shared on Reddit and other platforms, the event was held at an old plantation. Kirkconnell wore a long pink frock that clearly resembled the wardrobe of an antebellum-style Southern belle. Additionally, the decorations at the event reportedly included Confederate flags, which carry a strong connotation to the history of slavery. This incident caused fans worry about Matt James. It also saw the public question Kirkconnell's moral compass and her attitudes towards racism. 

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Matt James and Rachael Kirkconnell broke up before their relationship really began

Following Rachael Kirkconnell's "Bachelor" scandal, the Season 25 winner took to Instagram. "At one point, I didn't recognize how offensive and racist my actions were, but that doesn't excuse them. My age or when it happened does not excuse anything. ... I am sorry to the communities and individuals that my actions harmed and offended," she wrote, in part.

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As for Matt James, he struggled to come to terms with the news. On one hand, he had fallen in love with this woman; on the other, she had participated in a party that he found to be morally reprehensible. As he juggled his feelings, James realized that there was only one thing he could do — end things with his partner. 

On the "After the Final Rose" television special, James explained his thought process to Emmanuel Acho. "As someone who grew up in the South, [seeing those photos of Rachael] takes me to a place that I often try not to think about," the leading man shared. "When she spoke out and publicly acknowledged that she would do better and she apologized, is when I was finally able to take a check on myself and see where I was at, and I wasn't OK. It was in that moment and the conversation that I had that — Rachael might not understand what it means to be Black in America" (via CBS News).

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After the breakup, many viewers assumed that Matt James and Rachael Kirkconnell were unlikely to get back together. The scandal the pair had confronted seemed enormous, and it appeared that James and Kirkconnell's values were not necessarily aligned. Despite all of this, the couple's story was not over.

Matt James allegedly wanted to meet another woman one night in Miami

Even after Matt James and Rachael Kirkconnell underwent a very public breakup, the two didn't lose their strong sense of mutual attraction. The former couple continued to build their friendship at a distance. And, as they talked more and more, they seemed to reach an understanding. During this period, one source close to Kirkconnell told People, "Matt and Rachael have FaceTimed every day since March, besides one week in between the finale and 'After the Final Rose' when they were processing the photos scandal." 

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For many fans, the exes' chatting seemed to indicate a possible reconciliation. In reality, however, James and Kirkconnell weren't there yet. Even as the duo spoke every day, James allegedly continued to express interest in at least one other woman. Speaking to "Bachelor" blogger Reality Steve in an Instagram Live, a woman named Grace Amerling claimed to have been involved with James in the weeks following the show. According to Amerling, James asked her to meet him in Miami "for the night." However, as she wasn't in the mood to go out, she turned him down.

If James was chatting up Amerling and Kirkconnell at the same time, this would serve as a massive red flag. As Amerling herself told Reality Steve, "It just didn't sit right with me. I just felt like Rachael was so in love with him" (via People).

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The couple struggled to define their relationship

When Matt James and Rachael Kirkconnell reconnected, they weren't initially sure what they were doing. Were they on the brink of getting back together, or were they just exploring a friendship? At the time, the answer to these questions appeared to change quite frequently — and depended on who you asked.

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Kirkconnell's friends seemed to think that she and James were rekindling their romance. When Kirkconnell traveled to New York to visit James, someone from her inner circle told People that the point of the trip was to "work on their relationship and be consistent about things — out of the public eye, until they figured everything out." However, a source from James' camp insisted to People, "They are not together. He supports her as a friend. He is not looking for a relationship."

Unfortunately for James and Kirkconnell, this dissonance was a warning sign. According to experts, it's important for people in any kind of relationship to be on the same page. As psychologist Mert Şeker, PhD, told Marriage.com, "The indispensable importance of being on the same page in a relationship affects the durability and depth of the emotional bridges between people." In his view, lacking this sort of agreement can negatively impact communication. Considering that Kirkconnell and James didn't even seem to agree on the nature of their relationship, the two were not necessarily set up for romantic success.

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Rachael Kirkconnell and Matt James got back together after an ultimatum

Despite everything they'd been through, Matt James and Rachael Kirkconnell eventually decided to get back together. Interestingly, though, the duo's transition from friendship to coupledom was not all smooth sailing. The way that James remembers things, he only agreed to start dating Kirkconnell again after she issued him an ultimatum. As he revealed on the "Pomp" podcast (via People), "She was like, 'If you're going to make this work, let's do it. But, if you're not going to make it work, I'm going to let you do your own thing. That's really all I needed. It was an ultimatum that I needed."

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At the time of the ultimatum, Kirkconnell and James seemed outwardly happy about getting back together. In the same interview, James even labeled his relationship with Kirkconnell "great." That being said, relationship experts warn that ultimatums are rarely the best way to get one's needs met in a romantic context. 

Dr. Molly Burrets, a psychologist who specializes in marriage and family dynamics, told Self that ultimatums can harm an otherwise healthy relationship. The reason? They force a certain outcome, rather than allowing things to evolve naturally. "You'll always know in the back of your mind that you had to leverage something as important as your relationship's future to get your way," Burrets said. For James and Kirkconnell, starting out with an ultimatum was definitely a red flag.

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They couldn't agree on marriage

If Matt James and Rachael Kirkconnell were out of sync at the beginning of their relationship, that dynamic only intensified over time. While Kirkconnell dreamed of a shared future, James appeared happy with the status quo. In 2023, James was asked by People whether or not he and Kirkconnell were contemplating an engagement. The former "Bachelor" star replied, "There's no pressure. Everything that we do is for one another, and that, I think, is what makes our relationship work so well."

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James may not have felt the need to take things to the next level, but some reports indicate that Kirkconnell felt differently. As a friend of the couple's told the U.S. Sun in 2025, Kirkconnell spent years hoping that her beau would pop the question. Apparently, she even asked James to propose. "I will say this, he wouldn't commit. She basically gave him an ultimatum to propose by the end of 2024 and that didn't happen," the insider said.

For James and Kirkconnell to feel differently about the possibility of a long-term commitment would mean that they never got on the same page about their shared goals. 

Matt James might have been leading Rachael Kirkconnell on

According to some sources, Rachael Kirkconnell did not just hope that Matt James would propose — she actually believed that he was ready for an engagement. Rumor has it that Kirkconnell was so convinced that James was ready to pop the question that she was caught off guard when it never happened. As one source close to Kirkconnell revealed in an interview with the U.S. Sun, "I really don't think she thought he'd still be dragging his feet all these years later."

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Interestingly, the source in question implied that there was a reason that Kirkconnell was expecting a ring. Apparently, in his private conversations with Kirkconnell, James seemed much more excited about getting married than he did in public interviews. Speaking the U.S. Sun, the same insider claimed that James had discussed engagement rings with Kirkconnell. He had also allegedly commented on things like wedding menus. As Kirkconnell's friend told the outlet, James' comments may have resulted in "years of dragging her along. She tried and tried. It's been really hard on her, she really cared and thought this was going to work."

James and Kirkconnell broke up suddenly

Even as more and more red flags emerged in Matt James and Rachael Kirkconnell's relationship, the pair continued to stick together. They went out to restaurants and traveled to gorgeous places like Honduras. As far as many of the couple's social media followers could see, James and Kirkconnell were stronger than ever. On December 5, 2024, Kirkconnell even took to Instagram to celebrate James' birthday with a sweet montage. "Happiest of birthdays to my best friend, my teammate, my sous chef, the man that has my whole heart. You fill it (and my tummy) with so much love and laughter, and I'm so thankful I get to dance through this life with you," she wrote in the caption.

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In mid-January, James shared his own lovey-dovey Instagram post of Kirkconnell enjoying a pizza in London. But just hours later, he shocked fans with a break-up announcement. "Father God, give Rachael and I the strength to mend our broken hearts. Give us a peace about this decision to end our relationship," he wrote. Unsurprisingly, his followers reeled with the quick transition between "happy couple" content and a separation announcement. Kirkconnell's sister, Trinity, made a comment on TikTok alleging that the split was just as sudden as it seemed. "Yea so they were still together when he was posting all that [pizza content] ... just to give some perspective on the timeline of things," she wrote (via Us Weekly).

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Rachael Kirkconnell reportedly felt 'blindsided' by the separation announcement

If fans of the "Bachelor" franchise were shocked by Matt James and Rachael Kirkconnell's sudden breakup, they were far from being alone. The people closest to Kirkconnell were also said to be caught completely off guard by the announcement. According to at least one source, they didn't even know that the couple was thinking about parting ways. Speaking to the U.S. Sun about this matter, one of Kirkconnell's friends shared, "Everyone is confused and still trying to get to the bottom of what happened but first and foremost, they're supporting Rachael and making sure she's okay." Apparently, Kirkconnell's inner circle "didn't know they were fully broken up" and found out about the split by viewing James' post.

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The same insider went on to say that James went behind Kirkconnell's back to go public with the couple's break up. "Rachael is being pretty quiet right now but I know she was blindsided by Matt's post," they said. "She didn't know he was going to do that and definitely wouldn't have approved of it if she did. And she thinks it's just as weird as everyone else does." According to these allegations, it's possible that the breakup announcement had a serious impact on Kirkconnell's emotional well-being. As Kirkconnell's friend told the U.S. Sun, "She's humiliated that's how the news came out." Even while they were splitting up, James and Kirkconnell might not have been on the same page.

Rachael Kirkconnell appeared to hint at infidelity being involved

When it comes to maintaining a healthy relationship, infidelity is never a good idea. And while allegations of cheating are not proof of guilt in and of themselves, it's safe to say that these whispers are rarely a good sign — especially if they come directly from an inside source.

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Shortly following her break-p from Matt James, "Bachelor" alum Rachael Kirkconnell shared a TikTok video that many fans interpreted as a subtle nod to her failed relationship, as the video in question showed a woman sneaking into a man's apartment. The caption read, "Actual footage of me breaking into my friend's man's house after finding out they cheated" (via Us Weekly). Although Kirkconnell's choice to reshare this reel did not necessarily indicate that James cheated, it did lead fans to wonder whether or not she was dropping hints about what all went down. 

Matt James may have viewed Rachael Kirkconnell as an influencing opportunity

Given the large number of red flags that plagued Rachael Kirkconnell's romance with Matt James, some fans may wonder why the duo stayed together for so long. Although it's certain that a few factors kept the two together, one person close to the couple claims that influencing deals likely played a role. Speaking to the U.S. Sun, the aforementioned source explained that James relied on Kirkconnell to make money on social media. "That's his business, that's his livelihood. And the reality is, his content without Rachael doesn't do as well with views and engagement so he is continuing to post as much as he can with what he has," they said.

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While it's impossible to prove whether or not these allegations are true, we do know that working with family members — or romantic partners — can be tricky. As Steve M. Cohen, Ed.D., wrote in a piece for Psychology Today, "There may be baggage in a family relationship, and this baggage will inevitably be brought into the workplace." For James and Kirkconnell, having their romantic relationship to be so intertwined in their finances might have been messy. Now that they have split, the interrelatedness of those two things could become even more complicated.

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