Erika Kirk’s relationship history is in the news now, even though most of the evidence related to it was scrubbed off social media. Before she married Charlie Kirk, she might have been engaged to Tyler “JT” Massey and was also at some point in a relationship with Cabot Phillips.
What’s surprising is that she has professional ties to Phillips, and he has been a friend of Charlie’s, too. Erika Kirk has been in the news over her dramatic public appearances, at a time when some expect her to grieve differently. However, she has turned to politics and her new role as the Turning Point USA CEO.
Now people are interested in knowing more about Kirk’s personal life after she had claimed she hadn’t dated anyone for five years before meeting Charlie. However, a clip where Erika is flirting and drinking on the Summer House reality show is also going viral.
‼️🇺🇸: THERE IT IS: ERIKA Frantzve KIRK WAS DATING CABOT PHILLIPS JUST BEFORE she met CHARLIE KIRK despite claiming being single.
Wayback Machine shows that Cabot and Erika SCRUBBED their Twitter profiles of the evidence.
It appears CHARLIE KIRK DID NOT KNOW because of the… https://t.co/fb1p6MCEx7 pic.twitter.com/28b3l3Nngp
— Diligent Denizen 🇺🇸 (@DiligentDenizen) December 16, 2025
Apart from this, a photoshoot with Tyler has also grabbed online sleuths’ attention. It looks like an engagement photoshoot as the photographer captioned it, “Prepping another couple’s gallery for delivery … you’re both amazing humans & I loooooved shooting with you. So much laughter and love, it was perfect.”
Erika had also confirmed her relationship with Massey in 2014, describing her ideal day with her “favorite human,” who’s also an “incredible boyfriend.” Coming to her connection with Cabot Phillips, who is a senior editor at The Daily Wire, the two are believed to have dated in 2017.
There were comments calling the duo lovebirds under their photo. Rumors about a romance between JD Vance and Erika also shocked people due to their onstage interaction. While Erika has denied any truth to these rumors, she also feels she does not need to address them. She has learned how to tune out the rumors and conspiracy theories about her.
Erika Kirk claimed she didn’t date anyone for 5 years before meeting Charlie Kirk.
Meet Cabot Phillips, her ex before Charlie. He wasn’t just Charlie’s producer, but a career conservative operator and now now Senior Editor at the Daily Wire and previously Editor in Chief at… https://t.co/jL4waEK7d9 pic.twitter.com/zz4VSNdgBv
— Truth_teller 🇷🇺 (@Truthtellerftm) December 17, 2025
Kirk’s supporters have come to her rescue on X as they defend her. One user posted, “Take a look at this, these are AI-generated. Also, if you’re ever taking art classes, they would especially have you sign your name on them!!”
Many people think the photos might be edited in some way. There are those who believe it, considering how evasive Erika has appeared to some critics. An X user commented, “Ouf, she should have really just stayed home with the kids grieving instead of the media tours.” Another one posted, “It’s actually starting to make a lot of sense, unfortunately.”
