Feature Stories

Instagram Influencer Caroline Calloway’s Infamous Tour Is Coming to Dallas

Caroline Calloway
Caroline Calloway Wikimedia Commons

Caroline Calloway's infamous workshop tour is making a stop in Dallas.

Calloway, an Instagram influencer who is known for sharing the most intimate moments of her life, has detailed her ups and downs, her relationships and her heartbreaks with lengthy Instagram captions for a few years.

The captions got her a book deal in 2015. Calloway signed with Macmillan Publishers for $500,000, but two years later, she announced on her Instagram that she was pulling out of the deal because she felt the outline was sexist. She's still repaying the publisher.

Most recently, Calloway made news for her workshop tour, which some people call “Fyre Festival 2,” a reference to a disastrous Caribbean party for celebrity influencers, detailed in new documentaries on Hulu and Netflix. A few months ago, Calloway, sitting in her iconic New York apartment, asked her thousands of followers on Instagram if they would be interested in a creativity workshop tour, where Calloway would spend a few hours with her fans to talk about boys, eat salads and learn how to be themselves. Fans were excited at the thought of meeting their favorite Instagram celebrity, so before anyone had a moment to blink, Calloway was booking flights for herself across the country and began selling tickets for $165.

After finding out one of her initial tour dates was in Dallas, we reached out to her asking for an interview and she enthusiastically replied. But soon everything started to fall apart.

Kayleigh Donaldson, a writer and podcaster, began to criticize Calloway’s workshop tour on Twitter. The Twitter thread detailing every misstep in Calloway’s tour planning started with the tweet, “That Instagram influencer I occasionally check in on because she's The Worst is now charging $165 for a 4 hour ‘seminar’ on how to be yourself.”

Apparently, Donaldson is skeptical of the notion that the path to self-enlightenment begins with an Instagram-created celebrity.

This developed into a thread of what Donaldson called “scammer updates,” highlighting the flaws in Calloway’s workshop. With nearly 20,000 Twitter followers, Donaldson tweeted her observations on the faulty planning and unreasonable ticket prices. She covered everything from Calloway’s last-minute venue booking, her inability to fulfill the promise of cooking for all the attendees and every other change of plans that came up in the tour.

Donaldson then wrote an article for pop culture and entertainment site Pajiba explaining why she believes the workshop is a scam. Soon after, Calloway gained the most press attention she has ever had in her life, appearing in headlines in New York Magazine, Buzzfeed, Vice, Refinery29, Business Insider and more.

Calloway couldn’t ignore the bad press and she canceled the tour.

“I was at work, and I got an email that I had been refunded,” said Lauren Sheldon, a longtime fan of Calloway’s who purchased a ticket to her Dallas tour stop. “I went on Instagram on her story and she said something about canceling the tour and something about Twitter. And I’m not on Twitter, but I was curious, and it was dramatic. So I went on and I found the thread that they were talking about, and I was like, oh snap.”

Yes, oh snap.

But like the resilient and brave Instagram influencer that she is, Calloway un-canceled the tour and invited journalists to see for themselves if it was a scam or not. New York Magazine reported it was not a scam and that seemed to be all Calloway needed to be back to herself again.

“It’s so nice to finally get you on the phone, we finally did it. How are you?” Calloway said to us on the phone Wednesday afternoon. “I’m sitting here with the team; we just did a full day of booking tour stuff. I actually wanted to call you, because I have some really great news, and that is the first two cities we’re going to come to are Dallas and Austin, literally starting with Dallas.”

That’s basically all Calloway was willing to give us. We weren’t able to get a full interview, because she explained that they already had a system set up in which they would charge reporters the full $165 to attend the workshop so that the reporters could get the whole experience and be treated like guests, and then get an hour with Calloway after the workshop to interview her. This is how New York Magazine and Forbes were able to interview with her. (Editor's note: We'll pass.)

Calloway said she would talk to her manager, but she cannot make exceptions and promise interviews to people when she already has commitments to speak with other media. But Calloway’s first stop outside of New York on her workshop tour will be in Dallas on Feb. 9. The location is to be announced. Tickets go on sale at 5 p.m.

Now we wait and speculate from the outside like everyone else. The big question her fans and enemies and all in between have been asking looms above us: Is it a scam?

Maybe it depends on what you expect. If you’re going for the orchid crowns and a homemade salad by Calloway and gifts and care packages and a professional workshop, maybe it is a scam. But maybe you’re a fan and just want to meet your favorite Instagram influencer and are willing to pay for it. Or maybe since the whole tour blew up and now that Calloway’s got a whole team running this with her, it’s becoming the experience she promised her fans in the first place.

All we know is we’ll be watching. From afar. With $165 in our pocket.
KEEP THE DALLAS OBSERVER FREE... Since we started the Dallas Observer, it has been defined as the free, independent voice of Dallas, and we'd like to keep it that way. With local media under siege, it's more important than ever for us to rally support behind funding our local journalism. You can help by participating in our "I Support" program, allowing us to keep offering readers access to our incisive coverage of local news, food and culture with no paywalls.
Isabel Arcellana has been writing for the Observer since spring 2018 and has been creating fake newspapers for her mom since she was 8. She graduated from SMU with a double major in journalism and fashion media. Her five guitars are named after High School Musical characters.