Erica Kirk’s Dating History: The Story That Keeps Changing

Erica Kirk has repeatedly claimed that she didn’t date anyone for five years before meeting Charlie Kirk. According to her, she avoided dating entirely while living in New York City because she saw how miserable it was through her roommate’s experiences. She said she didn’t drink, didn’t go out, and believed that if you wanted to attract a man like Charlie, you had to live a certain kind of disciplined, traditional life.

That was her story.

But a growing number of receipts now directly contradict it.

And once you start pulling on this thread, everything else begins to unravel.

The Claim vs. the Record

Here is Erica, speaking at a CBS News town hall on December 14th, saying she never dated during her five years in New York:

“I never dated here because I saw vicariously through my roommate how terrible it was… I don’t drink. I find it unproductive… If you’re expecting to marry someone like Charlie, you have to be the type of woman that will attract a Charlie.”

That statement is clear and absolute.

But the record tells a very different story.

Reality TV, Alcohol, and Public Dating

During those same five years in New York, Erica appeared on Season 3 of Bravo’s Summer House. Her scenes were filmed in August 2018 at a New York City bar and in the Hamptons.

In the footage, Erica is visibly drinking alcohol—directly contradicting her claim that she doesn’t drink.

So that’s lie number one.

But it doesn’t stop there.

Erica wasn’t just “dating for TV.” She was publicly involved with multiple men during that period.

Tyler “JT” Massie and the Mystery Child

One of those men was Tyler “JT” Massie, a professional baseball player. Erica referred to him as her “incredible boyfriend” in an interview with Arizona Foothills Magazine. Photos circulated online that looked very much like engagement-style shoots, leading some to believe they may have been engaged—though no public marriage records have been confirmed.

Then came a much more disturbing discovery.

Viral footage from one of Donald Trump’s first major rallies in 2015 shows Erica standing next to a man who strongly resembles JT Massie. Between them is a young girl.

This has led people online to speculate—purely based on visuals—that the child could be theirs.

That speculation intensified after an audio clip resurfaced in which someone involved in the event recalls Erica calling and saying:

“Hey, I was Miss Arizona. I love Donald Trump. Can I be involved?”

She was placed prominently behind Trump at the rally—standing alongside family members of event organizers.

And in the same frame, sitting in the bleachers below, is Tyler Boer.

That matters.

Tyler Boer: The Connector

Tyler Boer later became Chief Operating Officer of Turning Point USA in 2017. And just months after assuming that role, he allegedly orchestrated what Erica described as a job interview—which conveniently doubled as her first meeting with Charlie Kirk.

Erica herself described it this way:

She attended the opening of Turning Point’s first building. Tyler Boer told her, “You need to meet the CEO.” She shook Charlie’s hand briefly. Nothing romantic, nothing notable.

But later, she claims, Tyler sat down with Charlie and said, “We need to hire her.”

That hiring decision ultimately turned into a relationship, marriage, and—depending on who you believe—something much more calculated.

Kabat “Kitt” Phillips Enters the Picture

Before Erica was set up with Charlie, she dated another man—Kabat “Kitt” Phillips, a senior editor at Ben Shapiro’s Daily Wire.

This relationship is not speculation.

A resurfaced tweet from September 2017 shows Kitt posting a photo of himself and Erica on a painting date with the caption:

“Yes, we’re that couple that gets painting lessons together.”

That same month, there are photos of Kitt and Charlie hanging out together, playing basketball.

This creates a major contradiction.

Erica claims she didn’t meet Charlie until 2018 at a Turning Point USA event in New York. Yet her boyfriend in 2017 was already socially close enough to Charlie to be spending time with him.

So which version is true?

Why Was This Relationship Scrubbed?

After Erica married Charlie, every trace of her relationship with Kitt Phillips vanished from the internet.

Photos disappeared.
Posts were deleted.
Mentions were erased.

The issue isn’t that Erica dated before Charlie. The issue is that she repeatedly denied it—and then participated in scrubbing evidence that contradicted her story.

That naturally raises the question: Why?

The Phillips Family Background

Digging into Kitt Phillips’ background only deepens suspicion.

His father, Tim Phillips, was a powerful Republican operative and former president of Americans for Prosperity. In 2021, Tim Phillips was abruptly forced to resign over what the organization vaguely described as “personal impropriety.” No details were ever released.

Then there’s the church.

A Reddit user claiming to have attended high school with Kitt alleged that the Phillips family ran a cult-like megachurch in Leesburg, Virginia called Cornerstone Chapel.

Public records appear to support at least part of this claim: Kitt’s brother, Barrett Phillips, is listed on the church’s website as an assistant pastor in charge of middle school youth.

The Tattoo and the Symbolism

Online investigators also zeroed in on a tattoo Kitt has on the inside of his bottom lip—a slice of pizza.

By itself, this proves nothing.

However, Charlie Kirk himself had repeatedly claimed that “pizza” was used as coded language in dark criminal networks, a belief he shared openly on social media.

Again, this does not prove intent or involvement—but people understandably find it unsettling.

Romanian Angels and Pattern Concerns

Some users have also raised questions about Erica’s involvement with Romanian Angels, tying it into broader theories about trafficking and nonprofit fronts. These claims remain speculative, but they continue to circulate as part of the larger narrative.

The Bombshell: The Military Base Meeting

The most explosive allegation comes last.

Candace Owens previously claimed that Brian Harpole, head of Charlie’s security team, attended a secret military-related meeting two days before Charlie was killed.

Now, Candace says an eyewitness identified another person at that same meeting: Kabat Phillips.

According to Candace, she sent the witness a photo of Kitt Phillips and received confirmation:

“Yes, that’s the person I remember being at the base.”

Candace attempted to contact Kitt Phillips directly—multiple times—requesting an off-the-record conversation. She received no response.

She also noticed that Kitt was absent from Morning Wire—a show he regularly appears on—from September 4th through September 10th.

The Silence That Fuels Suspicion

If these allegations were false, critics ask, why not deny them?

If Kitt wasn’t at that meeting, he could easily say so.

Yet there has been no public response.

No denial.
No clarification.
No explanation.

And silence, in a case like this, only fuels speculation.

Where This Leaves Us

At this point, many online believe that everyone involved was a trained operative—and that this entire situation began the moment Erica was set up on that “job interview” date with Charlie.

That belief may be wrong.

But the contradictions, deleted history, altered timelines, and unexplained connections are real.

And they leave one unavoidable question:

If Erica lied about her past,
if relationships were erased,
if key figures overlapped in secret spaces,

what else hasn’t been told?

Because the deeper you go,
the stranger it gets.