Episode 131: Redefining Asian Matchmaking (and Pleasure) with Cassindy Chao
In this engaging conversation, Judy Tsuei interviews matchmaker Cassindy Chao, who shares her unique journey from a corporate career to matchmaking.
Cassindy Chao shares her journey from corporate banking to matchmaking. Together with Judy, they discuss the unique challenges Asian Americans face in love and relationships, from people-pleasing tendencies to stereotypes around desirability. Cassindy reveals her approach to matchmaking, which focuses on self-discovery, breaking free from cultural conditioning, and building authentic connections. They explore taboo topics like intimacy, boundaries, and pleasure, offering insights on how to shift from performance-based relationships to deeper, more fulfilling connections. This episode is a powerful conversation about love, vulnerability, and reclaiming one’s true desires.
More about Cassidy Chao:
Cassindy is a former Goldman Sachs and JP Morgan investment banker turned-expert matchmaker. She is the founder of Ancient Wisdom, Modern Love, and Boutique Matchmaking, matchmaking practices for family office clients, offering tailored matchmaking, date coaching, and strategic consulting. She Boutique Matchmaker is the official partner of the Family Office Exchange (FOX), a global community of wealthy families and their advisors focused on optimal family legacy wealth management. Her expertise has been highlighted in a variety of notable outlets, including Business Insider, the Real Love Ready podcast, AsianBossGirl, I Hate Dating Apps podcast, Bay Area Women Magazine, and VoyageLA. She has also been invited to speak on modern love at prestigious venues like The Harvard Club, the Museum of Chinese in America, and The Chief. Her insights and journey were featured in Janet Hanson's book, “More Than 85 Broads: Women Making Career Choices, Taking Risks, and Defining Success -On Their Own Terms”. Additionally, Cassindy is the author of the Amazon best-seller,“Ancient Wisdom, Modern Love”, a practical guide to modern dating inspired by traditional Chinese idioms, or "Chengyu." Philanthropy and community service is important and Cassindy serves on the Business Leadership committee for Asian Health Services in Oakland, as Co-President of the Wellesley College Asian Alumnae Alliance, Associate Board for the NY Asian Film Festival and the Board of Aascend for young adults on the autism spectrum. She is married with 3 young adults and is in the SF Bay Area, Los Angeles and New York City.
Sound Bites
"My whole goal is to find our authenticity and unlimit ourselves."
"We are best at love, sex, and making money when we feel validated, seen, and loved."
"To be a good lover, you have to feel empowered, safe, and not shamed."
"We limit ourselves far more than society ever could."
"Sometimes, it’s about taking baby steps to get comfortable with intimacy and pleasure."
"We have this fear of becoming 'bad women' if we embrace our desires."
"F*ck saving face about martyrdom. That blows. It’s not sexy. At all."
Takeaways
Cassindy transitioned from a corporate career to matchmaking.
Cultural expectations can create blind spots in relationships.
Self-discovery is crucial for healthy intimacy.
Vulnerability is key to meaningful connections.
Many Asian Americans struggle with boundaries in relationships.
Intimacy requires practice and open communication.
Understanding personal desires enhances sexual experiences.
Breaking free from societal norms can empower individuals.
Martyrdom in relationships is unproductive and unsexy.
Open conversations about intimacy are still taboo in many cultures.
Episode Highlights
00:00 Introduction
00:33 Cassindy's Backstory
01:29 College Matchmaking Success
01:59 Approach to Matchmaking
02:21 Love, Sex & Money
03:07 Blind Spots in Asian Clients
03:37 Overcoming Conditional Love
05:00 Performance Anxiety in Intimacy
07:16 Unwrapping the Gown: Intimacy Tips
09:26 Talking Openly About Pleasure
10:23 Confidence and Self-Love
11:24 Judy's Reflections on Cultural Conditioning
13:29 Plans for a Future Episode
13:59 The F*ck Saving Face Moment
14:21 How to Connect with Cassindy Chao
Links Mentioned:
Judy Tsuei LinkedIn
Judy Tsuei Instagram
Cassindy Chao, Ancient Wisdom Modern Love
Cassindy Chao LinkedIn
Cassindy Chao Instagram
There may be affiliate links included in this blog post.
Transcript:
Judy Tsuei (00:02.668)
Welcome to the F*ck Saving Face podcast where we're empowering mental and emotional health for Asian Americans and voices of color by breaking through taboo topics. Life may not always be pretty, but it is indeed beautiful. Make your story beautiful today.
As you can imagine, it was a little hard for me to find an expert to talk about step five. think for, I don't even think it's just communities of color. I think for so many people, we don't talk about sex or pleasure or any of those things. And I'm so grateful that Cassindy Chow was willing and able to join me. And this is just part one, because we had so much fun while we were talking.
that I hope if you want to hear more from her, you will email me hello at judytsway.com and you won't let me know that you want to bring her back because she's fantastic. So she's a former Goldman Sachs and JP Morgan investment banker turned expert matchmaker. She's the founder of Ancient Wisdom, Modern Love and Boutique Matchmaking.
which are matchmaking practices for family office clients, offering tailored matchmaking, day coaching, and strategic consulting. She's the official partner of the Family Office Exchange, FOX, a global community of wealthy families and their advisors focused on optimal family legacy wealth management. So she has all of this left-brained expertise, and then she has deep right-brained expertise as well. She's been highlighted in Business Insider, in Asian Boss Girl.
in Voyage LA and she's been invited to speak on this idea of modern love at different prestigious venues like the Harvard Club, the Museum of Chinese in America, and the Chief. And her insights were featured in Janet Hansen's book, More Than 85 Broad's Women Making Career Choices, Taking Risks and Defining Success on Their Own Terms. She's also the author of her own book, Ancient Wisdom, Modern Love.
Judy Tsuei (01:55.182)
practical guide to modern dating inspired by traditional Chinese idioms. And she really believes in philanthropy and community service. When you hear her interview, she's just so authentic, so very much herself. And that was probably one of the best things about it. And she's very, very clear. She's not at all a sex therapist or anything like that. But because of the topic that she deals with when it comes to matchmaking, being compatible on an intimate level is so important as well.
And so I love her breaking through the taboos and I hope you will love this conversation as much as I did. I have Cassindy here with me and I am very excited because I've never had a matchmaker on the show. I do know someone in San Diego who declares herself as a Jewish godmother, grandmother matchmaker, but I've never met an Asian matchmaker. And given our legacy of, you know, structured kind of relationships and not talking about relationships and all of that good stuff.
I would love to just turn it over to you to share your story and how you got started in this work. Sure. Well, thank you, Judy. I'm so happy to be part of your podcast. I I love your messaging. I love how you've really kind of shifted beyond like stereotypes. So I was like your typical again, you know, well, you know, well behaved Asian gal whole thing. And I turned out I hated it. I hated it every single part of the path. Like I wanted to go for basketball. My mom says I'm too short. I want to go for all these things. Right. So
You know, I did the thing. was a banker at Goldman Sachs, JP Morgan. Like I really climbed up the ranks, earned money, blah, blah. But I hated it all. And I really always loved people. And I was kind of bad at numbers. I like got a D in calculus, the whole thing. But I pretended, right? So my whole life pretending to be good at something. And I was okay, but not great. But I really loved people. And then in college, I had had the most fun matching over 100 couples at the Wellesley College Asian Association blind date, semi-formal.
was great. And I practically flunked that semester too. It so much fun. So I thought I could make this into a career, so I did. And honestly, it's been amazing. It is so much fun. I feel like I can make a difference. And especially as Asian Americans, we, just as people in today's world, we limit ourselves. So my whole goal is to find our authenticity and unlimited ourselves. That's amazing. And so what is your approach that you take with matchmaking? think, you know, isn't there the saying that
Judy Tsuei (04:20.014)
all we care about as humans is like love, sex and money. Those are like, you know, the key things that drive us. But what is your approach to matchmaking and to relationships? What's very personal. I I really spent a lot of time understanding each person about what makes people love them. Why do they hang out with them? But also, then I also asked about what kind of person they want to meet. And what I find is that, especially the smartest people, we people have a lot of blockers and blind spots, right? So my job in a way is to
figure out what the blind spots are because when you talk about love, sex, and money, it is so important. But we are best at love, best at sex, best at making money when we're feeling validated, seen, and loved. So it's really important to think about that. It's not just about picking a checkbox about who you should match with because that person can be really bad.
for your love life, really bad for your own, you're finding yourself and finding your path. And so when you work with clients, especially Asian clients, what are kind of some of the blind spots that you're talking about? mean, think culturally we all have baggage. I know I was not taught that it was okay to date. So I don't know how my parents expected to go from not dating to then getting married. And they definitely didn't talk about sex or anything like that.
I'm just curious as to what do you notice with Asian Americans who you work with? so many hangups, but lovable hangups. We start kind of maybe something, let's go from PG to X. So the PG side, especially for a lot of us, because we're a very matriarchal society, there's a lot about conditional love, so we're people pleasers. And also in our society here, we are the industrious types, or the viewed as.
And so I think part of that is unlocking that, right? And learning to draw boundaries, which is really hard and not feeling guilty about it. We always feel like, I want to draw boundaries and I couldn't do that. It's a lot of guilt, right? But what happens is it manifests itself in different ways. If you're not drawing boundaries, you get resentful, you get angry, right? And it shows up, right? Or another thing for a lot of us Asian-Americans is that
Judy Tsuei (06:22.862)
You know, there's a lot of stereotypes that we get boxed into. You know, you got the exotic Asian, you got the not sexy Asian man. And these are so, excuse my language, stupid, but yet it's there. And even if we say we're okay with it or we can deal with it, we still hurt underneath. know, that's when I look at old movies, I'm like, it's so cringe. And it just, hurts our shoulders. It hurts our soul. So now going into the X-rated part, which is the fun part.
You know, when we're not feeling safe, we're not feeling loved, we're not feeling validated, then it's all about performance and get anxiety. We get, you know, we put a lot on ourselves. That sucks. That stinks, right? And, you know, I think to be a good lover, you also have to feel empowered and feel safe and feel not shamed. And that's something our parents don't necessarily go into it with us because they, their own parents didn't go into it with us.
Yeah, so how do you encourage people to talk about the X rated things? I, from like an emotional standpoint, I think that we do learn through different resources that we have therapy and you know, all the self help and different coaches and whatnot, we can learn how to be more vulnerable, how to have more of those conversations, how to learn how to have healthier boundaries and understand it means that you're keeping things out as much as you're keeping things in.
I said before growing up, my parents wouldn't let us close the door and they wouldn't let us, well, we definitely didn't have locks on the door. And in our household, they did not keep anything that should have been adult conversation as adults. was like all, you know, just fluid open, like porous essentially where they were always talking about financial challenges and hardships or getting into huge arguments, like just in front of us and yelling and screaming and there was no none of that. So I think that we have.
in today's modern culture, understanding of like why boundaries and stuff are important or how to lean into vulnerability and like understanding shame thanks to Brene Brown and other people like that. But I think this other intimacy conversation, pleasure, desire, any of those things are still so taboo. And especially in our culture, I mean, I think with my female friends and we're all in our mid 40s and we will talk about it.
Judy Tsuei (08:37.09)
but it's interesting because it's still like money. Like people aren't like really open with it. So I'd love to hear your kind of take on that. so many things on here. Gosh, so many things to unpack. So I have a saying that you need to take home the guy or the gal and unwrap things, right? Because you don't know what you're getting yourself into, right? And so you kind of have to unwrap.
things, otherwise you're gonna be stuck, right? But also because our parents didn't necessarily show ways of affection in ways that are sensual and sexual, right? We didn't grow up with that model, you know, hugging and kissing, you know, but it takes practice. And I think part of it is taking little steps. Because I think if I said to my clients, okay, you need to go on a date without your underpants on, they would freak out at me, right? But it actually is kind of helpful sometimes. I love it.
because it gets your focus because now you're dating instead of talking about the resume and the accomplishments, you're twitching down there thinking, ooh, what would it feel like to have this guy in here? I'm sorry, I'm so bad. Don't apologize. I love it. That's exactly what we want to break through all the taboos to have the conversations. I think this is so great. I'm blushing. Okay, because there isn't a talent matchmaker, mama something something who basically counsels that. I said, what a
great idea, right? Yeah. But the thing is just don't do it, right? And the thing is though is you'll see that if you, even the husbands and wives, you go on a date three times and you, without your underpants on, you find that it's a little bit different. It changes the shift and it opens up things that you don't know about yourself that you might be scared of. think sometimes we as Asians are scared. What are we going to unlock? We're going to turn into hussies or we're going turn into bad women and return to all these things. But if it's with somebody who's loving, that's not bad, right?
bad, it's not taboo. it's almost like a practice. So that's one. Two is I think baby steps, like the baby steps of kind of talking about things with your partner or like this is what I really like and this is embarrassing to me, but I didn't really have an orgasm until well into my 30s. It's embarrassing. I learned how to practice being sexually active, but I was never about...
Judy Tsuei (10:54.114)
my own pleasure. It took me forever to even know what I wanted, right? And that's not good, right? So in a way, kind of need to know what it is that makes us really just go, you know, your hair stick sticking up and you're like, wow. And because if you think it's a bad cycle, if you're not satisfied, your partner feels unhappy, and it's a cycle, then they feel like you're judging them and they're not able to perform right when it's really not about that. It's more like
I don't f*cking know what makes me cum, right? And so part of it is that, right? Like I've talked to these, like as a matchmaker, I've talked to a of sex therapists and things like that. And some of them are like, my gosh, what guys like, because Cindy, I can make a woman cum just by talking to them. I'm like, well, that's just great, okay? That's just Danny, good for you. I'm not having you meet my clients because they're just awkward, right? How would I say this? hi.
Judy, you're my client. love you. I'm you find love. And I can introduce you a guy who could make you come to look at him. Like, what does that do for them? Nothing, nothing, right? What really is more important is about like having the confidence and self love of oneself to kind of go, well, what does it for me? Is it, I'm kind of a boo person. Like I need my nipples touched, right? Okay, whatever, right? And not feeling like, ooh, so embarrassing. But that's what makes it happen. Because then once you know what makes you do it or what makes you happy, then you can share that with your lover. And then that makes.
him or her feel like, damn, I'm so good. And then it's a win-win. Sorry, I talk a lot. No, no, I love it. And I think that that's so important because my therapist had said before, you don't do this Asian woman murder thing. And she was talking about life in general, like just like, it doesn't serve anybody to do that. And that's where a lot of like passive aggressive communication comes from a lot of, know, and I think everything that you're expressing, whether it's love,
in a relationship or love, like intimacy under the covers, like, or in a bathroom or wherever, in a public place, wherever you wanna have sex. I think it's about really understanding yourself first and foremost, and then also asking and advocating. Amen, Judy, amen, amen, my gosh. Yeah, because when you said like, you know, I don't even know what feels good or whatnot, because I grew up in this household that was so structured in so many ways of expectations,
Judy Tsuei (13:09.836)
I didn't know what color I liked. I ended up having an eating disorder because I was just trying to control the external circumstances to fall in line with whatever I was told I was supposed to do. And so if we are learning those behaviors from such an early age, no wonder we get to a place where, like you said, women are not having orgasms until their 30s because they just didn't even, it's like a performative.
outward again that martyr thing like let me do this for you and then not get yes my sense of satisfaction yes exactly like and we're reading I was I remember reading these books on like gay man's tips for how to like satisfy your lover or something okay I'm go practice all these things but like this is not really doing it for me
Okay, I'm gonna choke and I have a really strong sense of smell like my god. This is making me realize that I want to have a whole other episode with you. So listeners and viewers, if you want to have Cassidy back on, please let us know, leave a review, reach out to me. You can find me on all the socials at Judy Tway and let me know because I would love to have you back on. Today we are
you know, hitting up at the end of the hour. It's the holidays, like the wildness. So I always ask every guest, if you could say f*ck saving face about something, what would you say f*ck saving face about? F*ck saving face about martyrdom. That blows. Like, you know, that's not sexy.
And if people want to follow up with you, where can they find you? I love talking to people. am at www.awmlove.com, which is my website, or my Instagram is matchmakerkissindy. Love it. Thank you so much. All right, the holidays are upon us. And if you want more support in your business, so if you are a solopreneur,
Judy Tsuei (15:15.318)
an entrepreneur, person who is making a shift in your career. You want to build your personal brand and you really want to take ownership in your own hands, especially the way that the world is now, the way that our whole economy is looking. I really always want you to feel safe and secure and able to provide for yourself and your family. And I think that personal branding and being able to work through any mindset shifts and blocks.
are one of the ways to do that. So I had a very successful breakthrough session with a client during Thanksgiving actually, and was working with a divorced mom. And she's extremely successful in her career, wanted to figure out the next chapter. And I just love seeing people release their baggage, come alive, understand how they can show up more as themselves and to feel this.
unwavering confidence in being able to do so and being able to handle the things that come their way. If that speaks to you, know that you can book a complimentary call with me and we can talk about it. And that there's so much that I have to offer in regards to this strategic marketing component, as well as mindset coaching and all these shifts that we can create as communities of color, being a neuro linguistic programming master practitioner, being a coach.
having all of these skills that are basically taking the most excellent practices that are available today and combining it into a modality that I can bring to you. And that's exactly what NLP is all about. So if that speaks to you, please go to judytsway.com, contact me, and let's make your 2025 absolutely awesome. I look forward to hearing from you.
Judy Tsuei (17:05.112)
Thank you so much for listening to today's episode. If you'd like to support me and this show, please go to iTunes and leave your review. It means so much to me and it'll help others find this podcast. I'll catch you in the next episode. And if you'd like to stay in touch between now and then, please visit wildheartedwords.com and sign up for my weekly newsletter. I've had people share with me that it's the best thing to arrive in their inbox all week. Aloha.
Thank you so much for listening to today's episode. If you'd like to support me and this show, please go to iTunes and leave your review. It means so much to me and it'll help others find this podcast. I'll catch you in the next episode. And if you'd like to stay in touch between now and then, please visit wildheartedwords.com and sign up for my weekly newsletter. I've had people share with me that it's the best thing to arrive in their inbox all week. Aloha.
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Keywords: mental health, Asian Americans, Matchmaker, Dating, Love, Sex, Relationships, Boundaries, Stereotypes, Intimacy, Pleasure, Desire, Self-Love, Confidence, Coaching, Empowerment, Authenticity, Cultural, Connection, Anxiety, Taboos, Vulnerability
