Caroline Calloway made a name for herself as an accused internet grifter, a hot mess New York City party girl and, most importantly, the author of several memoirs — and now she’s giving Us dating advice.
“I think the best way to go on dates is four dates in one night,” Calloway, 33, exclusively told Us Weekly on January 29 while discussing her latest book, Elizabeth Wurtzel and Caroline Calloway’s Guide to Life.
“People are lucky if they go on four different first dates in a month,” Calloway told Us. “You can do this one night in a month and have the rest of the month to yourself. You can still be living a vibrant, healthy, romantic dating life, and still have time to be alone with your cat and watch TikToks.”
If multiple dates in a single evening sounds overwhelming, have no fear — Calloway, of course, has advice (for single girls who date men) on how to get it done. According to the author, if you spend “one hour with these men” starting at 5:00 p.m., you can call it a night by 10:30.
“Honestly, if you’re dating women, this is not how I would do it,” she added. “This is for women dating men. My thoughts and prayers to all my brave, brave little soldiers out there. But listen, this is how you have to do it.”
Caroline Calloway. US Weekly
Calloway’s guide to life is a revival of author Elizabeth Wurtzel’s out-of-print 2001 memoir The Secret Life combined with Calloway’s own writing and insights, providing readers with various beauty tips, lifestyle hacks, book recommendations and some very specific advice for dating. The authors’ combined “guide” is accompanied by illustrations from artist Sam West. (Wurtzel, known for books such as her confessional memoir Prozac Nation, died in 2020 from breast cancer. She was 52.)
Calloway rose to popularity on Instagram, but her story — and life — blew up when she became the subject of a 2019 essay for The Cut titled “I Was Caroline Calloway,” written by her ex-friend Natalie Beach, who recounted helping Calloway write a book proposal, ghostwriting Calloway’s Instagram captions, and discovering she had purchased thousands of fake social media followers. Calloway also got a six-figure book deal for a memoir titled School Girl but reneged on the agreement, which meant repaying her publishers a $100,000 advance.
Calloway, like Wurtzel, lived in New York City for a decade before relocating to Sarasota, Florida, in 2022. Calloway said she “always felt five Hinge dates away from being some bohemian, fun, clouded up, socialite wife that some finance bro could keep in a box,” before leaving the Big Apple — and its dating scene — behind.
“It’s my first time ever dating men where every man I meet, I feel very confident that my lifetime earning potential is larger than yours,” she told Us of her romantic prospects in Florida. “It’s a really strange feeling to have in the patriarchy, in a heterosexual space. When I date women, it’s different. It’s like we’re in the same boat.”
While there are definite differences between New York and Florida, Calloway’s dating advice doesn’t have a city limit.
“First of all, if you don’t have a good [dating] profile, just stop. There’s nothing I can do to help you,” Calloway told Us. “The rest of the advice doesn’t even apply because you actually have bigger problems you need to address first. You need to get good pictures — and for your first picture you actually need to treat yourself like a brand.”
She continued, “A dating profile is the place to flex. People think a dating profile is a chance to tell other people about yourself. No. A dating profile is a trap and it should be an effective one. You are not trying to tell these people about you.”
Instead of baring your soul on a prospective dating profile, Calloway says giving strangers “the easiest, lowest hanging conversational fruit” is the name of the game. And she would know — she says she hasn’t changed her “entire profile in years.”
“These men are so f—ing dumb,” she said, adding that all she needs to entice a would-be date is a “whole Scientology bit.”
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“There’s a prompt and it’s like, ‘What do you like?’ I just keep talking about Scientology,” Calloway explained. “I put it in the book so that people will have the actual source. Everyone sends me the same messages. ‘Let’s talk about Xenu or L. Ron Hubbard or Tom Cruise.’ Everyone just sends me the same message and it’s perfect.”
If single-and-ready-to-mingle readers focus on giving “people a way to talk to you,” Calloway said, instead of trying to “capture your essence or express yourself,” securing a date is literally as easy as following a script.
“You say this one message, which I have memorized,” she said, before apologizing to anyone who has ever received her go-to message. “I copy and paste this. It’s, ‘F—, period. So hot. Period. Text me and let’s get drinks this week. Phone number.’ This is what you say to reach out first.”
Calloway further encouraged users to make the aforementioned comment “on the least sexual thing on their profile,” like an “embarrassing Halloween costume” or a meme.
“You’re using this bedroom language and because men have little pea-sized animal cave brains, they just see that in the beginning of the message because Hinge shows you the beginning of the message,” she said. “So they’re scrolling, they’re looking for sex. They see this bedroom language. They’ll open your message. They’ll respond.”
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While the Scammer author stands behind her dating tactics, Calloway’s intentions have changed now that she lives in Florida and she’s been wondering: “How much do you need someone to understand you intellectually if they like you, like your company, respect your career, and they’re kind to you?” She admitted to Us, “Something I’m learning about myself is that it actually might be less important to me than I once thought.”
“I think I got confused by how much I value my own intelligence,” Calloway continued. “Even if some people think I am the dumbest b— out there, I actually think I’m quite smart and actually kind of a genius at certain, very specific things. I got [so] confused by how much I valued [that] in myself, that I thought it was something I valued in a partner. It’s actually not as important to me as I once thought it would be.”
Given her rise to internet infamy, Calloway is no stranger to negative attention. In December 2024, she turned heads after claiming to have slept with Luigi Mangione, the 26-year-old man suspected of shooting and killing United Healthcare CEO Brian Thompson. The validity of her statement has been questioned by social media users. (“Honestly, I’m still surprised what goes viral,” she told Us.)
Earlier in 2024, she made headlines for claiming she hadn’t slept with a man who could read “in two years” on a May episode of the “No Jumper” podcast, and again for refusing to leave her Sarasota home during Hurricane Milton last October.
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But for now, Calloway is happy being the “strangest person in [her] town,” even though she still claims to be “happier” when she’s in New York.
“Every city has things that it values,” she told Us. “New York City is a place that loves creativity. It loves oddballs. It loves eccentricity. It loves originality. It loves chutzpah. It loves courage. It loves hustle. It loves enthusiasm. All these things that I really like about myself, I feel like New York City likes about its residents. And so I feel like when I see the city skyline, my molecules settle back into place. But it is a really emotionally volatile place to live.”
“In Florida, it’s like everyday is the same,” she added. “It’s just like bleach, bright white sunlight and the sound of the ocean. I read my books and I do my work and nothing ever happens to me. I’m fully retired from the plot when I’m there.”
Elizabeth Wurtzel and Caroline Calloway’s Guide to Life is out now.
Reporting by Emily Zogbi
