What to Know
After listening to Erika Kirk’s CBS Town Hall, people have questions about her dating history. Before she married her late husband, Charlie Kirk, she spent a decent amount of time in New York City. During her CBS Town Hall, she said that she didn’t date anyone during that time — but some people online are convinced that she’s lying.
“When I lived out here, I was here for five years, I never dated here because I saw vicariously through my roommate how terrible it was,” Erika said. “Somehow, getting drinks was the replacement of having coffee and breakfast. I personally would rather have coffee or brunch with someone — I don’t drink, I find it unproductive.”
After she said this, people started sharing photos of her previous boyfriends.
According to the New York Times, Erika and Charlie first met at a Turning Point USA event in 2018. After that, he asked her to meet up when he was in New York City, where she was living at the time. And though she claimed that she didn’t date anyone in the five years leading up to that point, internet sleuths found reasons to doubt these claims.
These internet sleuths believe that Erika dated at least two different men during the time that she claimed to have not dated anyone. And while there’s obviously nothing wrong with dating other men before marriage, they were confused about why she would (allegedly) lie about her dating history — because what is the point of doing so?
One TikTok user shared her thoughts.
“Erika allegedly had two boyfriends (that we know of) in the five years before meeting Charlie…” TikTok user @Stephwithdadeets captioned a video on the topic. “the math isn’t mathing. Why lie?”
In the video, she pointed out that in 2018, Erika appeared on the Bravo series Summer House. According to the Daily Mail, Erika went out with Jordan Verroi while on the show, though they did not seem to date after that. But Stephanie and other people on social media believe that her dating history extends beyond Summer House.
Erika also commented on how her roommate’s dating habits were ‘strange.’
During the recent CBS Town Hall, Erika reflected on her roommate’s dating habits and said, “I always thought it was very strange how she would go to drinks with one guy and then go to dinner with another.” But Stephanie argued that this is really not that weird, and Erika didn’t seem to think so either. “I don’t think Erika found that strange because I think she did the same thing,” Stephanie theorized. “It’s called dating. No one’s bashing that, but I don’t know why she’s lying about it.”
Internet sleuths also discovered that Erika allegedly dated a man named Cabot Phillips in 2017. Photos and social media comments shared by Stephanie indicate that they seemed to be a couple. For example, Stephanie shared a photo that Cabot posted in 2017. In it, he and Erika held up paintings, and he captioned it with, “Yes, we’re that couple who gets painting lessons together.”
@stephwithdadeets Erika allegedly had two boyfriends (that we know of) in the five years before meeting Charlie… the math isn’t mathing. Why lie? 👀 #erikakirk #cabot #tpusa #charliekirk #greenscreen ♬ original sound – Stephwithdadeets
Additionally, Stephanie shared photos of Erika with another alleged boyfriend, Joseph Tyler (JT) Massey. Erika actually referred to JT as her boyfriend in an article for Arizona Foothills Magazine. In the piece, she wrote about her ideal day, which included, “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.”
According to photos shared via X, Erika and JT did a photoshoot together in 2015, suggesting that they may have dated within the period of time that Erika says she didn’t date anyone.
Some people found it very weird, but others defended her.
Erika Kirk again in a couples photoshoot with Tyler Massey in March 2015, well within the 5 years she is claiming that she "never dated" https://t.co/pfT2u4P5VG pic.twitter.com/PlG8KVH7KR
— Knoxie (@KnoxieLuv) December 16, 2025
Reacting to photos shared on X, one person argued that it’s only weird because Erika claimed that she didn’t date anyone during that period of time. “Nobody would even care if she just didn’t bring it up herself, the issue is that it comes across as deceitful when she made a point of it,” they wrote.
But others jumped to Erika’s defense, saying she only claimed that she didn’t date anyone in New York City. “She said she didn’t date in New York City because of how bad the dating scene was there. She dated in Arizona,” someone else argued.
