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.

Speaking & Events

Making Effective Connections in 2025

RECENT

SPEAKING

Events

SPECIAL EVENTS & TALKS

2nd Edition Book Launch

2nd Edition Book Launch

2nd Edition: Shared stories, recipes and more

Ancient Wisdom, Modern Love:

Chinese Wisdom for Dating Success

Matchmaker Cassindy Bestselling Book

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.

CASSINDY FEATURED IN

Best Asian Matchmaker

Matchmaker Cassindy and her team serve the San Francisco Bay Area, Los Angeles Metropolitan, and Greater New York City for our clients providing them bespoke asian matchmaking and dating concierge services.

And it’s not just for love, we bring people together for friendships, networking and plain old fashioned fun.

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