

Today we’d like to introduce you to Dana Hamilton.
Dana, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
The path to my current career started when I had to drop out of college due to an eating disorder. I took a semester off to focus on recovery and when I came back to NYU, I decided to transfer to the smallest school at the university, Gallatin, so I could enter a program where I could make my own major. I settled on writing and nutrition/food studies because I wanted to write eating disorder recovery material.
After graduation, I worked in the NYC book publishing industry editing books at HarperCollins and Hachette, including my dream humor project, “Suck Less” by RuPaul’s Drag Race alum, Willam Belli. I loved helping people tell comedic stories and soon realized I could tell my own.
I left publishing so I could write for magazines–somber pieces about eating disorder recovery for SELF Magazine and Teen Vogue, but also a lot of funny essays about dating in NYC for New York Magazine, VICE, Cosmo, Marie Claire, and many others. Six months after I started out as a freelance writer, I became a sex columnist for Playboy. My work took me to a lot of interesting places, including furry conventions, naked yoga classes, and even a nudist swinger’s resort in Jamaica! I also road-tripped across the country and back by myself for a year in 2018 to see what the dating culture was like in 6 different U.S. cities. I started posting screenshots of me talking to people on Tinder on my Instagram and that’s when my career trajectory started to change.
On the road trip, I was having the time of my life dating in a bunch of different places and documenting it on social media. Soon, my followers started coming to me to ask how the heck I came to love dating and have so much fun with it. That’s when I realized all the skills I learned in eating disorder recovery are what helped me develop a very positive relationship with dating. I also started to realize just how much the diet industry and the modern dating industry had in common; both are industries that capitalize on and reinforce the concept of scarcity mindset, competition with others, and low self-esteem.
I started using my Instagram to talk about sex, dating, relationships, body image, and eating disorder recovery (and how they all intertwine). That’s how other diet culture dropouts started to find me and ask for help reframing the way they think about dating (a slog, overwhelming, or a “waste of time”) to how I think about dating (FUN, not that serious, an opportunity to have great life experiences and learn a lot about yourself). Earlier this year, I launched a Patreon where I publish essays for anyone who wants to learn how to build the sex and dating lives they deserve. I had been approached many times to teach sex/dating skills and had done it unofficially (and sporadically) over the four years I’ve been a sex columnist for Playboy. But it wasn’t until the people reading my work on Patreon started creating a huge demand to work 1-on-1 with me that I realized I could transition to coaching full-time. I made the leap in April and never looked back.
As an anti-diet dating coach, I help “my people”–diet culture dropouts who identify as women, non-binary, or trans men–develop the skills necessary to become amazing at dating. I teach how to build the mindset, communication skills, and self-confidence necessary for dating to be something that enriches your life–all with a heavy dose of humor along the way.
Has it been a smooth road?
I am floored by the demand for my services and struggle to keep up with it! The waitlist to work 1-on-1 with me is quite long, which is why I’m planning to start including group coaching in my offerings by the end of the year. So far, I’m working on the creation of courses like “How to Break Away from Goal-Oriented Dating” (goal-oriented dating is the concept of “I want a partner or NOTHING AT ALL”- type thinking) and a body image bootcamp for people who’ve experienced narcissistic abuse (a very common experience among my clientele).
We’d love to hear more about your business.
I specialize in helping anyone who’s struggled with their relationship with food, exercise, or their body learn how to build the sex and dating life they want and deserve. When most people come to me, they are at their breaking point with dating. Dating makes them incredibly anxious or they avoid it altogether for a myriad of reasons, like believing dating apps are a waste of time, fearing rejection, or just plain being unsure of how to date without launching themselves far into the future (i.e., putting engagement rings on their Pinterest board after a first date).
With me, a Playboy sex columnist, as their wing-woman, I offer clients lots of hands-on support and powerful mindset work. I co-write dating app bios and help choose profile pictures, offer 1-on-1 swiping support, and help clients initiate meaningful conversations on apps (no more “I don’t know what to say!” on my watch!). A big part of my job is helping clients sharpen their communication skills so they feel more comfortable advocating for what they want/don’t want (including co-creating scripts for important conversations re: safer sex practices, personal boundaries, and how to “let someone down gently” after a date where there’s no chemistry). When it comes to mindset work, I help people dismantle scarcity mindset and goal-oriented dating so they can enjoy the process of dating instead of hyper-focusing on finding a partner, overcome dating anxiety, and heal their self-image.
What sets me apart from other dating coaches is my humor and “real talk” approach. I don’t believe dating is serious (after all, it’s supposed to be fun!) or a search for “The One.” The idea of “The One” is BS, especially in a place like Los Angeles where there are millions of people to build an amazing relationship with! That kind of scarcity mindset pedaled by other dating coaches is incredibly damaging; it makes single people feel like they’re failing or not searching hard enough. I also define dating success by the quality of the experiences clients have while dating, instead of the quantity. I consider three amazing dates in a year to be far more successful than 30 “meh” dates.
What I’m most proud of are seeing the changes in my amazing clients over the time we work together. I can’t tell you how amazing it is to see someone come to me in tears during our first session and leave a few months later with a renewed sense of purpose, higher standards for themselves, and a new way of thinking about dating.
Is our city a good place to do what you do?
My business is fully remote, so I’m sure it would do just as well regardless of where I was geographically, but I will say this: Los Angeles is the best city to date in. Hands down, no question. So in that regard, I will say it helps me draw upon a lot of inspiration by being in a place that’s full with a lot of amazing single people.
Contact Info:
- Website: DanaHamilton.com
- Instagram: Instagram.com/dana_hamilton_
- Twitter: Twitter.com/dana_hamilton_
- Other: Patreon.com/DanaHamilton
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