Best Asian Matchmaker
Speaker | Matchmaker | Author
MEET CASSINDY
Cassindy Chao is a third-generation matchmaker, former Goldman Sachs and JP Morgan Securities investment banker, and tech executive turned premier relationship expert. With a deep understanding of both human connections and high-stakes finance, she blends tradition with modern insights to help professionals find lasting love.
Her matchmaking journey started early—at Wellesley College, she orchestrated a wildly successful mixer for over 100 students, setting the stage for her career. Today, Cassindy is recognized as the top matchmaker for Asian professionals, working with high-achieving clients, including CEOs, doctors, and artists, to navigate the complexities of modern dating.
Beyond matchmaking, Cassindy is the author of Ancient Wisdom, Modern Love: Chinese Wisdom for Dating Success, where she combines Eastern philosophy with practical dating advice. A sought-after speaker, she has delivered sold-out talks at venues like the Harvard Club of New York, or the Museum of Chinese in America, captivating audiences with her insights on love, relationships, and personal branding. She is frequently invited to speak on guiding ultra-high-net-worth families in discussions about dating and marriage, as well as navigating modern relationships with a cultural lens.
Deeply committed to her community, Cassindy serves as Co-President of the Wellesley College Asian Alumnae Alliance, a Development Committee member for Asian Health Services, and an Associate Board Member for the New York Asian Film Festival.
When she’s not matchmaking, speaking, or writing, you might find her playing a fierce game of mahjong (yes, she’s also a mahjong teacher!), making homemade Taiwanese foods, or planning her next adventure—always with great relationships in mind.
500+
Happily ever afters
50+
Events
2000+
Largest Singular Audience
How it Works
It is important to understand that matchmaking is an in-depth and very personal process that requires a significant commitment of time and resources from our team. Because of this we review applications carefully and choose to work with only a select group of clients at any given time. Once you’ve completed our basic application and indicated an interest in our matchmaking service, a client service team member will reach out and schedule time to get to know you better, discuss your goals.
Once our contract is finalized, the fun (for you) and the dedicated work (for us) begins.
We’ll ask you to complete a detailed questionnaire that will help us get to know you better. Then we’ll move on to a 1:1 meeting (ideally, in person) where you will have Cassindy’s complete focus to review your answers and begin to build the profile of the person you are seeking – from physical attributes and personality traits to religion, ethnic identity, values, and passions. We explore wishes and wants, must-haves and deal-breakers.
We have resources available to assist with photo shoots, personal styling, date curation, and can even arrange practice dates.
Matchmaker Services
CASSINDY FEATURED IN
Ancient Wisdom, Modern Love:
Chinese Wisdom for Dating Success
SECOND EDITION: SHARED EXPERIENCES, STORIES, AND BONUS FAMILY RECIPES.
LEARN HOW LESSONS FROM “CHENGYU” CAN CHANGE YOUR LOVE LIFE FOR THE BETTER WITH WARMTH AND HUMOR.
For centuries, Chinese people have been distilling everything from philosophical ideas to folk wisdom to advice on relationships into short, memorable, and often humorous sayings called “chengyu” (成語).
These ancient phrases and their relatable wisdom that I myself heard growing up are a core part of my matchmaking practice as I advise my clients on successfully navigating dating and building relationships.
TESTIMONIALS
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CASSINDY’S IMPACT
Discover how cassindy helps individuals and organizations build great relationships