Today we’d like to introduce you to Ruby Le Wynn.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
Since I was young , I’ve always wanted to make a difference, and as I grew older, I knew I could only succeed in a career if I was passionate about it.
I knew I wanted to work in the dating and love industry since high school (yes, many thought I was crazy…). I had this natural fire, passion, to help people with love. So, even against my Asian family’s disapproval, I took the steps to do so.
I earned a Masters degree in Marriage and Family Therapy from USC and a Bachelors degree in Social Work from SDSU. I worked with many couples to enhance their overall satisfaction and overcome struggles in their relationship. But, it was there that I realized many couples should not have been together in the first place. Then, I began the journey to help singles find the right person for them.
I worked with the matchmaking firm, It’s Just Lunch, and I was the lead matchmaker and coach at eHarmony’s premium service, eH+. I have helped hundreds of clients search for their special person, coached those to be successful on dates, and helped clients get happily married and in relationships.
It was during this time that I noticed the big problem society was creating the label of “nice guy” – popularly known as the man who gets in the friend-zone. However, what I saw was the good-hearted man who hasn’t been given the chance. With the inspiration from brothers who I watched get stuck in these situations, alongside the largest positive impact I made with these type of clients, I decided to branch off on my own with the mission to help the “good gentleman” find their confidence, strength, and charm to find the right partner… all without changing who they are. On top of that, the idea of working for myself because of freedom was a no-brainer.
Now, people know me as the Modern Day ‘Hitch’ – I am dedicating my time to these men unleash a part of them to get the right ladies drawn to them. Now, almost a decade of having my business, and helping hundreds of singles find their partners, get many married… this is where I truly feel I’m making the biggest difference.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
It was a long road of sudden turns and course correcting. When I initially embarked on this business adventure, I was going through large personal life adjustments. Leaving my corporate job with 3 months of savings to make something happen, a canceled wedding that lead to an emotional change of home, and moving back to my home city (of San Diego) into my parents home (not an ideal scenario for an adult). I was dealing with such emotional turmoil and change, but I was driven and determined to make my dream a reality.
I took a business online course, and even did a mastermind retreat from that same coach. I learned so much and got my first client. However, though I knew I wanted to be a dating coach, where I am now took some pivoting. I started as a dating coach for everyone, men and women. But after initial tests, I realized it was challenging to market. And, something just didn’t feel right.
A light bulb went off in my mind as I reflect on my past work with clients (through eHarmony, and matchmaking), who did I enjoy working with? Who did I truly help? And then…looking at my personal life, who was I around when this passion to help singles come up? Who did I want to help?
Then, It came to me… I grew up with two brothers. Both of them, I wanted to deeply help and hoped they’d find the love they deserved. Because I grew up around them, I thought quite logically and structurally about dating. Then, in the work I past did, I remembered hearing “Ah, it’s really helpful you’re a woman, I understand that other perspective because of you”
But, even when I focused on wanting to help only men, and shifting my marketing to that, I ran into another issue…
My message was still vague, and I’d get plenty if inquiries that didn’t lead to clients because we weren’t the right match. It wasn’t about the sales for me, it was about making sure I could make an impact. So, back to the drawing board, what else?
And after testing and reflecting, that’s how I cam to realizing — I wanted to help good-intentional, introverted, men who wanted a long term healthy relationship (not picking up women, not trying to up their count of women they’ve dated)
Once I had that on lock, it was full speed ahead!
Nothing is ever smooth though, but once a focus is clear, it makes the other bumps more manageable because I always came back to my purpose.
From Facebook Ads suddenly not working, my website getting hacked, my cloud hosting taking my site offline for weeks, my funnels failing, Writers block (or “content block?”), and more — though those moments fill me with anxiety, I push through it (with support!) cause I love what I do. And nothing is going to stop me from it.
As you know, we’re big fans of Good Gentleman. For our readers who might not be as familiar what can you tell them about the brand?
I’m Ruby, some call me the modern day Hitch. I’m the dating coach for you know, the good guys.
I’ll help men build their confidence so they will attract the right woman without changing a thing about them. I believe they have the strengths, they have what it takes…they just need to bring it out. No false bravado, no B.S. They will no longer have that “nice guy” label hanging over them and instead be the GOOD guy that they’ve been looking for.
With almost a decade of experience as a private dating coach as well as working with It’s just Lunch and eHarmony, I help them do something about this.
I have la carte products guiding them through specific topics like how to write your online dating profile, how to gain confidence, finding their attractive traits, and more. This is where most should begin if they don’t know where to start and need a boost!
For those wanting something more personal & faster results, I provide private coaching customized to their personality and needs as I hold them accountable, as they quickly reach your results.
I call this my Good Gentleman private premium 1:1 coaching package. A high-touch service customized to their needs and meet their goals without changing who you are.
What would you say have been one of the most important lessons you’ve learned?
That my mental and spiritual health is everything. It is the foundation of what allows me to take on any challenge, grow, adapt, and flow. With a business, it’s easy to focus on the to-do list, on the actions being taken next (asking “what now? What’s next?”), to continue to work, work, and work, and to focus on the dollars.
But, I’ve realized that my main strength that brings the most happiness and success, is when I take care of myself. The time I make sure to carve out for practices that ground me and bring me joy, is even greater than writing an email campaign. Because when I am at peace and feeling expansive, I get the best ideas and work through tasks faster.
So, the lesson I’m keeping, is to make sure I schedule time every day to do things like journal, pray, walk, meditate, teach and play with my daughter, connect with friends, do yoga, enjoy the harbor/ocean view, and more.
Contact Info:
- Website: https://goodgentleman.com/
- Instagram: https://www.instagram.com/rubyloveadvice
- Facebook: https://www.facebook.com/GoodGentlemanAdvice/
- Youtube: https://www.youtube.com/rubyloveadvice






