Matchmaking
Services
Publications

Ancient Wisdom

Publications

Matchmaking

Services

Events

Love Quiz

Ancient Wisdom

Publications

Matchmaking

Services

Events

Love Quiz

Ancient Wisdom

Chicago

Asian Matchmaker in Chicago

Matchmaking for Chicago's Finance, Law & Medical Professionals

Cassindy Chao Featured In


Cassindy Chao Featured In


Cassindy Chao Featured In

Begin Your Journey

Bespoke Intention & Lasting Love

Not ready to speak directly?

Begin Your Journey

Bespoke Intention & Lasting Love

Not ready to speak directly?

What a Goldman Sachs Banker Learned About Love | Matchmaker Cassindy at GMF

AWM Love brings personal, discreet Asian matchmaking to Chicago’s accomplished singles — from the Loop and River North to the Gold Coast, Lincoln Park, and out to the North Shore. Private, handcrafted introductions for traders, attorneys, physicians and executives who want something real and don’t want to find it on an app. My clients come from every background, and a meaningful share of my matches are cross-cultural.

My Tie To Chicago

My connection to Chicago runs through the work. I spent years at Goldman Sachs and J.P. Morgan, and anyone who has worked in that world knows how tightly New York and Chicago are wound together — the desks talk constantly, people move between the two cities their whole careers, and the derivatives world here is its own gravitational center. I know those people because I was one of them.

I have made many matches in Chicago - especially with my ties to professional organizations such as the National Association of Asian American Professionals and previous ties to the Family Office Exchange. I have worked with many executives at FOX and also did a podcast with FOX Ceo Peter Moustakerski and also a webinar for them.

Credentials

I’m a third-generation Chinese matchmaker (紅娘) and a former Goldman Sachs and JP Morgan investment banker. I’ve been featured in Business Insider, NBC News Daily, and ABC News. I bring both the ancient wisdom of the 紅娘 tradition and a very modern understanding of the lives my clients actually lead.

Who I Work With In Chicago

It All Starts With Learning About You and….Who You’d Love to Meet.

My Chicago clients are traders and quants, attorneys at the big firms, physicians and academic clinicians, consultants, founders, and executives across finance and professional services. Many are Booth or Kellogg alumni. A good share are first- or second-generation, balancing demanding careers against family expectations that never quite go unspoken. They are direct, unpretentious, and tired of the app churn — Chicago people generally say what they mean, which makes them a pleasure to match.

Not all of my clients are Asian. A good share are people whose lives already cross cultures — who’ve worked in Asia, whose careers are international, or whose families already are — and who want a partner who moves comfortably in that world. The cultural fluency those matches take is something I pay close attention to.

Why Dating Here Is Harder Than It Should Be

The trading day and the billable hour own your calendar. Markets open early, deals close late, and the years compound. It is the same structural trap I saw constantly in banking: the work is genuinely urgent, and your personal life is the only thing with no deadline.

Your circle is your firm. Desk, practice group, service line, residency program. The people you know are the people you work with, and dating inside that is complicated for obvious reasons.

Chicago is a big city that dates like a small one. The professional world here is more connected than outsiders expect. Word travels through firms and alumni networks, which makes discretion matter more than people assume.

The winters make it easy to disappear. It’s simple to go quiet from November to March, and then again the following year. Momentum is genuinely hard to maintain here, and a lot of good intentions dissolve into another season indoors.


SAN FRANCISCO MATCHMAKING

What a Goldman Sachs Banker Learned About Love | Matchmaker Cassindy at GMF

Client Success Story

One of our clients was a lovely woman finance executive who had relocated from the Bay Area to Chicago. She met many terrific men and worked out at the East Bank Club yet had a hard time responding in kind when she knew someone was interested. So we went back to the basics and worked on simple flirting tips. It was fascinating that a woman who was so fit, attractive and accomplished would be oh so bashful in real life. But that was only a temporary hurdle and within weeks she was actively dating and successfully to find the right partner in life.

Couple relaxing in a Chicago park beneath the skyline

FAQs

Do you serve the suburbs and the North Shore?

Do you work with people in trading and finance?

Are there enough Asian-American singles in Chicago to make this work?

How is this different from a dating app?

How much does an Asian matchmaker in Chicago cost?

Do you only work with Asian clients?

A PRIVATE NEXT STEP

A PRIVATE NEXT STEP

Still deciding?

My background is unusual — third-generation 紅娘, Goldman Sachs and J.P. Morgan, Wellesley, and 35 years of doing this. It's also what makes me good at the specific thing I do, which is connecting exceptional people. But being effective isn't enough on its own. There has to be fit, and there has to be care. If you don't feel that when we talk, I'd rather you know it early — and so would I. The first call is free, and it goes both ways.

Years of setting up Great Dates

Matchmaking Testimonials

Cassie has been a matchmaker since her college days at Wellesley. She helped me identify my now husband. He is my one true love. He understands, accepts, and celebrates me. Without her sage advice, I would not be married today.

S.C. & M.D.

Matched Couple

Married

Getting married during the pandemic was an adjustment and we made it work. Now you can add another success story to your list!

P.L. & R.S.

Matched Couple

Married

Our backgrounds were very similar, and we had a lot in common, yet we would not have met without her nudge. We fell in love the day we first met and we’ve been married ever since. Cassindy is our trusted friend for life!

K.S. & B.N.

Matched Couple

Married

  • Cassie has been a matchmaker since her college days at Wellesley. She helped me identify my now husband. He is my one true love. He understands, accepts, and celebrates me. Without her sage advice, I would not be married today.

    S.C. & M.D.

    Matched Couple

    Married

  • Getting married during the pandemic was an adjustment and we made it work. Now you can add another success story to your list!

    P.L. & R.S.

    Matched Couple

    Married

  • Our backgrounds were very similar, and we had a lot in common, yet we would not have met without her nudge. We fell in love the day we first met and we’ve been married ever since. Cassindy is our trusted friend for life!

    K.S. & B.N.

    Matched Couple

    Married

Featured In

NBC News Daily — Oct 2025
Everybody needs to have a dating portfolio

NBC News Daily — Oct 2025 Everybody needs to have a dating portfolio

Business Insider — How a Goldman Sachs Banker Became One of America’s Top Asian Matchmakers

NEWSNATION — Feb 2026 — We need to be open to meeting someone special

10+

Years of setting up Great Dates

Years of setting up Great Dates

40+

Events & Gatherings

Events & Gatherings

Events & Gatherings

60+

Happily Ever Afters

Happily Ever Afters

Happily Ever Afters

Our Services

Luxury Matchmaking Services

Luxury Matchmaking Services

Signature Service

Date Concierge

Get dating strategies and solutions to help improve your success. Ideal for post-divorce or difficult break-up situations, and unsuccessful dating patterns.

Personalised Strategy Sessions

Dating Profile Refinement

Ongoing Coaching & Support

Premier Service

VIP Matchmaking

Our premier service offers quality bespoke introductions. In-depth and personalized process requires our dedication and resources on behalf of our clients.

Curated Bespoke Introductions

Curated Bespoke Introductions

Dedicated Matchmaker Relationship

Dedicated Matchmaker Relationship

Comprehensive Compatibility Review

Comprehensive Compatibility Review

Begin your journey to a meaningful and lasting connection

Begin your journey to a meaningful and lasting connection

A PRIVATE NEXT STEP

A PRIVATE NEXT STEP

Ready to make room for someone remarkable?

Ready to make room for someone remarkable?

We help our clients find extraordinary matches and often move beyond old expectations, stereotypes, habits and blockers and make sure they are ready for their last (and best) relationship.

We help our clients find extraordinary matches and often move beyond old expectations, stereotypes, habits and blockers and make sure they are ready for their last (and best) relationship.

You must be at least eighteen (18) years of age to access or use AWM Love ("Service"). By using the Service, you represent and warrant that you are at least 18 years old and have the legal capacity to enter into this agreement.

You must be at least eighteen (18) years of age to access or use AWM Love ("Service"). By using the Service, you represent and warrant that you are at least 18 years old and have the legal capacity to enter into this agreement.

You must be at least eighteen (18) years of age to access or use AWM Love (“Service”). By using the Service, you represent and warrant that you are at least 18 years old and have the legal capacity to enter into this agreement.

You must be at least eighteen (18) years of age to access or use AWM Love (“Service”). By using the Service, you represent and warrant that you are at least 18 years old and have the legal capacity to enter into this agreement.