Interview with Chloe Gray, Founder of Dating Advice by Chloe

Michelle Whiting
5 min readDec 20, 2021


Image Credit: Chloe Gray

Chloe Gray is the founder of Advice by Chloe, a company that specializes in providing premium dating consultancy services. Since its inception, Advice by Chloe has helped thousands of clients polish their dating profiles, improve their match rates, go out on dates, and navigate relationships.

To learn more about Advice by Chloe or to book an appointment, visit their website here.

Here we sit down with Chloe, to know a bit more about her journey as a dating consultant.

Q. What inspired you to become an entrepreneur?

Chloe: Does necessity count? Back when I was still a college student I wasn’t able to find a job quickly enough to pay my rent. I ended up posting to Reddit with an offer to help people improve their dating profiles. It went viral and then snowballed into a full-blown business. It was almost an accident; I’d never had any interest in being a business owner. I had planned to work for an organization as a therapist after finishing school, but I soon realized that I’d rather use my therapeutic skills as a dating consultant rather than traditional counseling. This was completely outside of my comfort zone, but I’ve loved every minute of it.

Q. How did you get started?

Chloe: Before Advice by Chloe, I was pursuing my master’s degree in clinical social work and working full time to get me through school. My employer moved away, and I wasn’t able to find another job quickly enough to pay rent. I was selling my things, eating ramen for weeks on end, and had $0.33 in my bank account. My landlord was leaving eviction notices on my door and my utilities were on the brink of being shut off. I was terrified. I decided on a whim to post to Reddit with an offer to review people’s dating profiles, hoping to earn enough money to buy groceries. Within a few minutes I had dozens of responses, and within a few weeks, I had gone viral across several platforms. I decided to start taking it seriously, made a business plan, started conducting research, and Advice by Chloe was born.

Q. What was your biggest startup challenge? What steps did you take to overcome it? What did you learn?

Chloe: The content of my services was never a challenge. I really enjoyed every moment of putting it together. I’m a clinical social worker and a researcher at heart — so studying algorithms, collecting data, and working with clients is my happy place. The real difficulty was literally everything else. I’ve had to become an “expert” on so many topics overnight. Setting up a website, figuring out LLCs, taxes, pricing and scheduling, social media, and deciphering the world of marketing are all things I never thought I’d need to do. It took a few sleepless nights (and enough coffee to kill a unicorn), but I got there.

Q. What is the Most Memorable Thing You’ve Done Since you Started your Business?

Chloe: The first time I had a celebrity as a client was probably the most exciting day of my life. It felt like Advice by Chloe had finally made it. I’ll also never forget the first time I went viral, the day I decided to quit my job as a therapist to focus exclusively on Advice by Chloe or reaching the point that I was able to buy a car with cash. I burst into tears the first time I sat in my new car. I named her Coco Cruze and I love her. It’s still mind-blowing to me that just two years ago I had eviction notices on my door.

Q. What is one book you recommend, and why?

Chloe: Oh gosh, just one? If I can only choose one, it’d be Marketing Made Simple by Donald Miller. It was easy to read, had step-by-step instructions for beginners, and helped me tremendously when I was first starting out. If I can choose more than one — Half The Sky by Nicholas Kristof if you want to help change the world, The Hobbit when you’re craving a bit of adventure, or The Humans by Matt Haig when you need to restore your faith in humanity. Reading is my addiction… that, and video games, hot coffee, and Critical Role.

Q. What are your top 3 favourite online apps, tools, or resources and what do you love about them?

Chloe: Reddit is definitely my favorite since that’s where I got my start! It’s a wonderful and complex community and I’m so grateful for the support they showed me when I was just starting out. Loomly for social media management. I’ve tried so many different apps to manage my social media and Loomly makes my life a million times easier. Last but certainly not least: Discord. I spend most of my day on Discord. It’s where I meet a lot of my clients, it’s where I host my book club, my D&D campaign, voice chatting while playing video games, or having watch parties. I started a Discord server for Advice by Chloe and it’s become a wonderful community. Discord for President 2024.

Q. In terms of legacy, what is the mark you’d like to leave on the world?

Chloe: Studies are showing that dating apps are having a pretty negative impact on our mental health and self-esteem. I honestly can’t count how many of my clients come to me feeling unattractive, unvalued, lonely, and helpless to change their situation. A big part of the problem is a fundamental misunderstanding of how dating apps work and how to market yourself effectively. Dating apps are a marketing campaign, that’s all they are. Your success on them is largely a reflection of your ability to market yourself effectively. It is not a reflection of your value as a human being, your desirability as a partner, or even your level of attractiveness.

I want to dispel the pseudoscience, fostered dependence, manipulation tactics, and shady shiz that is so prevalent in my field. Advice by Chloe isn’t pickup artistry and it isn’t predatory. It’s actionable advice based on current psychological research, human behavior, and an understanding of the dating app algorithms. Human beings are social creatures. We need companionship in order to thrive. It’s really important to me that Advice by Chloe is truly helping people fulfill that need.

Q. In one sentence, what’s the best advice you’d give to someone just starting out on their entrepreneurial journey?

Chloe: “Just keep swimming.” Running your own business is going to be filled with ups and downs, complications, impossible tasks, and the occasional tax audit. It’s easy to get stuck in a cycle of panic or reactionary behavior but resist the urge. Think big, think ahead, do what you do best, ask for advice from people you trust, accept help when you need it, protect your brand, and most important of all, don’t lose sight of your vision.

To keep up to date with Chloe and her journey, connect with her on Instagram



Michelle Whiting

Copywriter, publicist & entrepreneur. Passionate about sharing empowering and informative stories from thought leaders across the globe.