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An Interview with Cherlyn Chong – Dating Experts Month

Tell us about yourself. What makes you a dating/relationship expert?

My name is Cherlyn and I help high-achieving professional women get over their exes, take their lives and careers back and finally find love again. I’ve been doing this for 4 years and it’s been such a pleasure seeing my clients get in beautiful relationships and get engaged.

How does your approach differ from other experts?

I take on a science and behavioral psychology-based approach. Because of this, I’ve been able to predict with 99% accuracy, within the first two dates, if a man is likely to stay on or break up with a client. My approach is also very results-based, not time-based. I usually don’t stop until you are actually dating a great guy.

To ensure this, I am always applying high-performance techniques and logic into a client’s dating journey, so that they are able to bounce back quickly and enjoy their dates. Speed and efficiency is the name of the game.

What are some of the biggest challenges/frustrations you see from the people you work with?

The biggest one is that they can’t trust men anymore. They are so jaded from past marriages that they think all men are selfish, conceited and always going to take away their power. 

Another big frustration is that bad men seem to always get away with everything with no consequences, while they, the good person, always seem to be left with the heartache.

Member submitted question

I’m 49, female and recently divorced. I met my husband when I was a teenager so I’ve never really done the whole dating thing. Where do I start?

– Catherine, 49

First, yourself. Yes, that’s so cliché, but dating just isn’t very effective without first being comfortable with singlehood. Without that, we’re very likely to put all our expectations for happiness on a man, leading to emotional upheaval if anything goes wrong. 

So take some time for you, it’s OK not to rush this process. Only go into dating when you feel like you want to share your life and happiness with a man, not when you want a man to give you happiness. Huge difference.

Then, assume the identity of a short-term pessimist and a long-term optimist. That way, you have very realistic expectations of dating while still believing in your eventual success. 

Ease into dating slowly. Start with online dating, and learn how to write a good profile and how to take good, stylish photos that show off your best features. Of course, if you want to cut short this process, get a good expert in to help you. 😉

Do you find any patterns with respect to what women are attracted to? What are the main things women are looking for in a man?

Do you find any patterns with respect to what men are attracted to? What are the main things men are looking for in a woman?

Yes, women tend to have a “type” and tend to go for men with similar traits, which can be good or bad. I find that women are always looking for men who have an edge… someone who isn’t boring and whom they don’t have to mother.

Member submitted question

I’ve recently started an age-gap relationship with a woman who’s 15 years older than me. I haven’t told anyone about us yet and she’s getting annoyed, almost like I’m ashamed of her. I really like her but I just don’t know how my friends and family will react. What should I do?

– Marv, 30

Ask yourself what’s the worst case scenario that can happen due to your friends and family overreacting. Then ask yourself if you are willing to deal with that for the sake of your relationship. If it’s no, then it’s time to take a closer look at why you’re in this relationship to begin with.

If it’s yes, then plan to tell them gently. Show them why she’s the woman for you. They might not like it, but they can respect your decision if you’re truly genuine about it.

How can people connect with you on social?

Specially for the Toyboy Warehouse women, I have prepared a bonus 30 min video about the science of how successful career women can stop dating toxic men and get to the right man who will adore them:

People can also follow me on Facebook: or join my Facebook Group: if they want to get over the wrong man.

Finally, what’s the one piece of advice you hold close to your heart?

The best thing you can ever do for yourself is to only take advice or support from people who are also getting their ass kicked and people who already have the thing you want. 

So if you want to be in a relationship with a good man, get a mentor who already is in a healthy relationship. You don’t deserve to be judged, you deserve to be understood. Surround yourself with your tribe, and you’ll shine.

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