Life, Values & Legacy: Our Chat with Ruby Le Wynn of San Diego, CA

We’re looking forward to introducing you to Ruby Le Wynn. Check out our conversation below.

Ruby, really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: What is something outside of work that is bringing you joy lately?
I have a 14 month old baby and becoming a mom has been such a rewarding, fulfilling, and chaotic (haha) additional part of my life. I used to call my business my baby, bringing me all the joy and crazy I could ask for. But after having my daughter, I’ve then noticed I could have more of everything and do more of everything. Her smiles, laughter, growth, and the quality time I have with her and my husband gives me new joy and a new sense of purpose.

Can you briefly introduce yourself and share what makes you or your brand unique?
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.

Amazing, so let’s take a moment to go back in time. What did you believe about yourself as a child that you no longer believe?
In elementary school, I’ve realized I was always the smallest, physically, in my class. Additionally, I was very shy, I barely spoke. Because when I spoke, I was made fun of. I’d only love to speak to teachers and focused on the assignments. So, I was always picked last for every P.E. activity, and for every group assignment. I believed I was weird, odd, and the weakest link of any group. I accepted being “small” and that because I had those limitations, there was a limit of how far I could reach in goals.

But, year and year, as a I grew older, I found my passions, my strength, and voice, I let go of that belief. I realized I could be small, but mighty. My weirdness and quirkness could make me unique to achieve what most can’t do. My voice mattered, and I could be loud for the causes I’m passionate about. I actually don’t have limitations. I could achieve anything I wanted to.

If you could say one kind thing to your younger self, what would it be?
To be her most authentic self, and that is how she’ll achieve everything she’s ever dreamed of. To do her best every day, and that was enough. No need to listen to anyone else, just listen to her inner voice and it’ll guide her to do what feels right. And even when it feels like everything is crumbling, it’s meant to happen so it can make space for the greater things that will come.

I doubt myself at times til this day, always thinking I could be farther along than I currently am. But, then, I look at what I had….and I realized, the life I’m living is what my child self dreamed of. I’m currently living the dream, because at a point in my life, I decided to be my most authentic self and pursue what I genuinely felt passionate about.

Sure, so let’s go deeper into your values and how you think. Whom do you admire for their character, not their power?
My grandpa passed away in 2018, and he was apart of my whole childhood. He lived with me, took care of me, and was someone I admired. He was the most kind soul, genuinely caring of all walks of life (people, animals, plants, and all), patient, and a man who continued to do good. His purpose was to spread peace, positivity, and do good. He was always present and calm. I truly looked up to how he moved in the World.
Little did he know, because of his generosity and his character, he had strong power. I want to continue his legacy in making a good impact in the World, prioritizing family, and living mindfully.

Okay, so let’s keep going with one more question that means a lot to us: Are you doing what you were born to do—or what you were told to do?
I feel grateful every day that I am doing what I truly felt I was born to do. I’ve always said from a young age of 5 years old that I wanted to help people. when I was a child, I was told the best way to do that and the only way to do that is to be become a doctor.

I had the goal to become a doctor until I was in college and realized that it was not my passion, and that there are many other ways to help people.

I truly believe that my current work was even given in my birth name. Ruby is a gemstone of red, love, and passion. Doesn’t that sound like a date coach? (I’ve had may clients wonder if this was my real name) I was born for this!

It’s fulfilling to help people — While I’m helping single men put themselves out there, I’m also helping single women hopefully find these emotionally intelligent kind men.
Seeing my clients gain such incredible confidence in themself, find the love of their lives, and even get to witness families expanding. What better way to help the world, but to add love to it in my smallest way that I can?

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