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Episode 57 | Dating Coach: Ruby Le



Picky is really focusing on characteristics and qualities that don't actually correlate to a happy relationship.

Below is an abridged audio transcript of Episode 57 from Season 4 of Rock The Boat: Making Waves, edited for clarity.


Dating these days is tough for everyone, but when you start considering race and identity it becomes much more complex. When you factor in some of the statistics that you see, you can tell that there's a discrepancy between Asian men dating in the United States versus Asian women dating in the United States.


Asian Americans are the largest group to marry outside of our own race. A 2017 research study showed that one out of three Asian American newlyweds had a spouse of a different race or ethnicity. Of the 30% of Asian Americans who married outside of their race, Asian American women are twice more likely to marry outside of their race than Asian American men are.


In this episode, Lucia talks to dating coach and TEDx presenter Ruby Le about dating in the Asian community. Some of the topics include:

  • How Ruby got into matchmaking and working as a dating coach

  • What she encounters with her clients who are Asian as well as other races

  • The difference between being selective and picky

  • What advice Ruby has for people trying to date now

The following is an abridged transcript of the episode. To listen to the full episode, find us on Anchor, iTunes, Spotify, or wherever you listen to podcasts!


I. Meet Ruby


Lucia: To help answer some of my questions and to dive deeper into the challenges both men and women face during dating, I invited Ruby Le, a professional dating coach on to rock the boat.Ruby owns her own practice and has a master's in marriage counseling. She has successfully helped hundreds of people take steps towards finding love. What caught my attention about Ruby was actually her TEDx talk. Here's a quick clip.


Ruby: We're going to get personal today because we're going to be talking about your love life. That's right. Not mine, yours. I know. It's such an exciting topic. I can hear your responses now. What love life, Ruby, where all the great men, where all the great women, dating is hard. Relationships are hard.


I want to share with you a quick story. I had a client, he went on his first date and he came back to me and reported how it went, and I can already tell he was really excited and he tells me, "Ruby, that was one of the most amazing days I've ever been on. She's passionate. She has a lovely smile. We got along so well. We connected, we had chemistry, we had so many common interests, but I'm not going to see her again."

Okay. So I waited for him to proceed. Tell me why. And he tells me, "Ruby, her hair is like, Medusa."

Okay. I've never heard that before. So I challenged him to go on a second date with her because bad hair is something you can fix or work with.


My mistake was that I didn't tell him the step by step approach and how to fix the issue because what ended up happening was on the second date, he ended up taking her to the hair salon where he had a set appointment already for her. And. Oh wait for it. And he already talked to the hairstylist and showed the hairstylist a photo of the hair he wanted her to have.


Yeah. Ooh, bad move. Exactly. So as you can guess, she never saw him again. This client ruined all chances he had with this fantastic lady because of the issue he had with her hair. And I will tell you that after that he had a really tough time finding anybody else even close to her personality or even close to that connection.


Lucia: After hearing her TEDx talk, I reached out to Ruby to schedule some time over the phone. During our talk, Ruby opens up about her choice to become a dating coach, to the chagrin of her parents. She also touches upon some common themes she sees while coaching both men and women around dating and the silver lining to dating during the pandemic.


Ruby, I'm so excited to have you on Rock the Boat. Tell me about your journey.


Ruby: I actually started this, believe it or not, in high school I, I was really intrigued by dating and relationships, and this came after. I had like my really awkward phase. Of when I didn't talk to anybody, I was really shy. And when I finally started going to like different high school clubs, I started kind of interacted with different people.


At that time, I was just feeling intrigued by relationship dynamics. I started kind of Googling about it and then I asked myself, you know, is there a career in this? And obviously my Asian parents are like, no.


My current title is a dating coach, but I think in Asian world, they don't really know what that is. They don't really understand even therapy. but when you say a matchmaker, they're like, "Oh, okay."


Lucia: When you said like your parents didn't really approve of it, did you guys talk about reasons why?


Ruby: It really is about their thoughts on the actual career. So I first brought it up to them because I wanted to change my major out of biology. So that's when I was first brought it up and I got my bachelor's in social work, right? And then I got my master's in marriage and family therapy. And it was that point where they said, why therapy?


Because people only go to therapists if there's something wrong with them. And if you become a therapist, there's something wrong with you, and you'll kind of fall into that. And so that was their biggest concern. I grew up in a household where we didn't really talk about feelings or anything like that either.


II. Making the match

Lucia: What was the first successful match you made?


Ruby: I worked with so many people. It's so hard to remember the first successful match. But I do remember all the matches that have really just made me so happy. And I remember, it's because of this match is when I realized I wanted to be a dating coach and that I wanted to do this on my own and in my own business.


And I remember, I think he was 45 years old. Never had a date, never had a girlfriend. Asian, came in very skeptical, very insecure of himself, and he really thought this wasn't possible for him. Like he really, really thought that love wasn't in the cards, but he really wanted to try. He wanted to make sure he tried everything he could, and helping them through that process.


And this was kind of the first client I really, really coached, after helping him develop his confidence and everything. And I introduced him to this one lady. I will always remember. He tells me, "She is the greatest cause she actually loves me for all the reasons why I didn't love myself."

That was really powerful for me and that's when I recognized I really wanted to help the good guys. That's kind of what skyrocketed what I'm doing.

Lucia: What were some of the things that you were helping to coach this guy with? I mean, to your point, he was 45 and he's never dated anybody before. I'm sure there's a lot to work through. What was that process like?


Ruby: I think a lot of it is in regards to shifting his mindset and thinking that what he has somebody else doesn't want. I think the biggest thing that I had to work on was making sure we worked on his internal obstacles and how he views himself more than worrying about what others are probably viewing him as.


III. Asians in the dating world


Lucia: I want to talk about like the dating dynamics for Asians. Statistics show that Asian women are desirable to men of all races versus Asian American men are undesirable to women of all other races except for Asian.


From an interracial dating perspective, with the men that you're coaching, do you have men who specifically want to date Asian women or do you have men who want to date other women of other races but feel that they can't?


Ruby: Most of my Asian clients that come to me, this discussion always happens because they're curious, and I always tell them that I'm not going to deny those statistics, like OkCupid has created it, that is there.


But it is also important to note that that is not all, because I feel like a lot of people see that data and think, "Oh my gosh, this is the world. This is everybody." When honestly, it took and captured research at a certain time, and obviously with only one online dating site.



Now I'll always say, is it still happening around us? Yes. It's a hot topic because people are now wondering why, and there becomes this anger now from Asian males is seeing these Asian females being with white guys.


And I think the biggest thing that creates that anger is not being able to see what the root of that is and the reasoning for that.


After observing hundreds of clients, this includes personally even my own girlfriends. I've recognized that like Asian males, obviously same as Asian females, were raised with certain expectations and rules.


Culturally, I think a lot of males are taught to be respectful, quiet, don't speak on your feelings. It's not about what you want. You are to follow what your parents are saying and what they want. So they carry this identity obstacle for a long time. Like, what group do we belong in? Right? There's always that question.


I think generalizing can be very unhealthy cause I always say have all of white male clients who had the same struggle with they're really reserved. They're really shy. They're really awkward. They don't know what to do. And that's because their parents, were very restrictive of them.


Lucia: So what about the people who are like super picky? Do you have clients that are extremely picky and you have to kind of help them work through their pickiness.


Ruby: Yes. Oh, those are my favorites. I say those are my favorites because we have quite a big discussion, in those regards. And that's actually why you mentioned my TEDx talk. That's actually why I talked about that. I kind of talked about how people have these lists, lists of things that they really want.


And when they're really picky, I always tell them that it's okay to be selective, but you still want to select the person that would be right for you and compatible with you.


But picky is really focusing on characteristics and qualities that don't actually correlate to a happy relationship.

Show Notes


This blog post is a short version of the transcript. Listen to the full episode to get all the details of Lucia's conversation with Ruby and more real examples that came up.


We hope that this episode has got you thinking more about the state of dating and how it relates to identity. It's a deeply interesting but also painful topic for many people. We could all do better by questioning our biases and examining our thought processes when considering potential people to date.


You can find Ruby Le at her website Good Gentleman. You can find Ruby’s Tedx Talk on YouTube.


For further reading:

Listen to the full episode on Anchor, iTunes, Spotify, or wherever you listen to podcasts!

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Rock The Boat is a podcast elevating the stories of Asian leaders, founders, and pioneers in their fields. Through candid and thoughtful conversation, the host Lucia Liu uncover stories of their upbringing, Asian identity, and the movements they've built. 

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