Who Was Erika Kirk With Before Charlie? Her Relationship History Is Causing A Stir

Erika Kirk's dating life is all people want to know about these days. Rumors about the Turning Point USA CEO's relationship with Vice President JD Vance nearly eclipsed headlines about the tragedy of losing her husband, Charlie Kirk, who was assassinated on September 10, 2025, at a Utah Valley University rally he was hosting. Now, folks are desperate to know about her past relationships with two men, one of whom is in Erika's professional life today.

During CBS News' "A Town Hall with Erika Kirk," the former Miss Arizona revealed that she did not date while living in New York City for five years before she met Charlie in 2018. Of course, there is the viral clip of Erika's brief cameo in Bravo's reality series "Summer House," which shows her drinking and flirting during the summer of 2018, just before she claimed to meet Charlie. Now, internet sleuths have done some digging and are speculating that not only was Erika dating at that time, but that she may have even been engaged, as well.

On December 15, a picture from 2015 of Erika and a man named Tyler "JT" Massey went viral on X, formerly Twitter, that appears to be engagement photos. However, some users on Reddit have pointed out that she could have simply been modeling for the Arizona-based event photographer, Luna Bear Studios. That doesn't appear to be the case, though, considering the photograph was part of a social media post from the studio, which tagged both Massey and Erika and wrote, "Prepping another couple's gallery for delivery ... you're both amazing humans & I loooooved shooting with you. So much laughter and love, it was perfection."

Then there's the fact that Erika herself confirmed her relationship with Massey in an article for Arizona Foothills Magazine tracing the chronology of her "ideal day," writing, "5:30 p.m.: Happy hour with my favorite human and best friend, JT Massey, also conveniently enough my incredible boyfriend." The article seems to date back to November 2014. If that wasn't bad enough, netizens found photos of Erika with Cabot Phillips, the senior editor of The Daily Wire, but his presence in her past has a deeper meaning.

On December 15, another person on X posted a video containing possible evidence that Erika Kirk had a purported relationship with Cabot Phillips (pictured with Erika above) before she met Charlie Kirk. The video showed Erika and Phillips' interactions on X between June and October of 2017, revealing comments that referred to them as a couple and as "love birds." Curiously, Phillips worked for the major conservative institution, The Daily Wire. While neither her supposed engagement with JT Massey nor her relationship with Phillips has been confirmed, the rumors have been enough to convince many skeptics.

‼️🇺🇸: Did you know that Erika Frantzve Kirk apparently used to date Cabot Phillips Editor of the DAILY WIRE in 2017 just a year before she met Charlie? 🤔

The posts are now scrubbed but the replies to them are still there on Erika Kirk's (old now locked) Twitter profile. 👀... pic.twitter.com/Vw21YlqGdH

— Diligent Denizen 🇺🇸 (@DiligentDenizen) December 16, 2025

What shocked people even more was that Phillips had already led several events for Turning Point USA on campuses across the country. As such, some folks are suspicious of Erika's speculated romantic connection and its transition into a professional relationship. In reality — per his Instagram — Phillips seems to be happily married and was actually a friend of Charlie's.

Nonetheless, Erika has made it pretty clear that she has mastered the art of tuning out the rumors and conspiracies. While alluding to affair rumors about her and JD Vance, Erika told Fox News that she hears Charlie's voice in her head saying, "'Baby, just stop. Stop. You don't have to answer to every single person that's accusing you of things or saying that you're doing this or grieving a certain way.'" Considering this new information, the accusations won't end anytime soon.