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At 29, Erika Kirk crossed paths with her future husband, Charlie Kirk, during what initially seemed to be a job interview but quickly morphed into a romantic encounter in September 2018. Prior to Charlie entering her life, Erika had lived a full life, complete with past relationships. Among those was Joseph Tyler Massey, a name that has recently caught attention due to resurfaced photographs on X, formerly Twitter. These images hint at a possible engagement between Erika and Massey, suggesting Charlie wasn’t her first significant other.
Dimitrios Kambouris/Getty Images
The details surrounding the end of Erika and Massey’s relationship remain unclear. However, Massey’s Facebook page indicates he is now happily married with two children, a parallel to Erika’s life, as she shares two children with Charlie. A self-identified aunt of the photographer who captured Erika and Massey’s engagement photos confirmed the pair’s past engagement, albeit these claims remain speculative without Erika’s confirmation.
There’s no public record to suggest Erika had been married before Charlie, though the rumors of her engagement to Massey have certainly sparked curiosity. Some have humorously questioned her past: “Wait … is she a black widow? How many men have died after mating with her?” one user joked on X. Others have dismissed these speculations, questioning the significance of her past relationships: “This isn’t a wedding photo or something? Is it breaking news that she has an ex bf??” another user commented. Ultimately, the discussions highlight the curiosity surrounding Erika’s romantic history without suggesting any overlap with her marriage to Charlie.
I promise it will be unbiased and no emotion injected, and just historical, but I want to have all the information correct.
I’ve never done this in 17+ years on this account but if you have… pic.twitter.com/fuG7RiqFW3
— Erin Elizabeth Health Nut News🥜 (@unhealthytruth) December 14, 2025
To be fair, it isn’t like she kept it a secret; Erika openly talked about her ex-boyfriend in a feature for Arizona Foothills Magazine describing her ideal day. “5:30 p.m. Happy hour with my favorite human and best friend, JT Massey, also conveniently enough my incredible boyfriend, talking about everything, from his day at the baseball field to the latest with his music group, Saving Southern,” she wrote. According to MiLB, Massey was born in Chattanooga, Tennessee, and played professional baseball for many years before retiring in 2016. Apparently, he’s also quite religious. “11 p.m. If I can get my brain to turn off, it’s bedtime. JT and I have a nightly prayer tradition where we take turns leading the bedtime prayer. Tonight’s my night,” Erika said.
It’s unclear exactly how their relationship ended, but his Facebook profile shows that Massey has moved on and is now happily married with two children. (Erika also has two kids with Charlie.) Meanwhile, a woman who has identified herself as the aunt of the photographer who shot Erika and Massey confirmed that the exes were indeed engaged to be married. But unless Erika confirms this story, which is highly unlikely, it’s all purely speculative.
Fans react to Erika Kirk’s romantic past
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Was Erika Kirk really married to someone else before her marriage to Charlie Kirk? According to public records, there’s no actual proof that she had tied the knot with anyone else prior to Charlie, yet her rumored engagement to Joseph Tyler Massey sure has stirred the pot. Some were quick to poke fun at her romantic past: “Wait … is she a black widow? How many men have died after mating with her?” one quipped on X. Another said of Erika, “I’m glad she experienced having an attractive partner at some point.” But others don’t see why her rumored engagement to Massey should be an issue. After all, it wasn’t like there was an overlap. “This isn’t a wedding photo or something? Is it breaking news that she has an ex bf??” a third user argued.
However, there were also those who couldn’t help but notice the strange similarities between Erika’s ex-boyfriend and Charlie. Reacting to an old photo of the exes, taken in 2014 during Phoenix Fashion Week, an X user pointed out, “I cannot explain it, but that first picture is the face template of Charlie Kirk,” to which someone else agreed in the comments: “He looks like a better version of Charlie.”
Tyler Massey & Erika Frantzve (Kirk)
– October 9, 2014 pic.twitter.com/jyI5YgT6GN— FrauHodl (@FrauHodl) December 14, 2025
It’s all interesting online gossip, but at the end of the day, none of it matters to Erika, who has repeatedly stated that Charlie was, and will always be, the only man she’s ever truly loved. “I can’t help but smile when I hear his name or say it,” the Turning Point USA CEO told Fox News’ Jesse Walters months after her husband was slain. “He was the love of my life,” she adds. “[He] still is.”