Dating Insights & Advice

Expert matchmaking advice, dating tips, and stories from Matchmaker May.

Asian professional man in a refined lounge setting, seated thoughtfully by a window, representing a calm and introspective approach to modern dating and meaningful relationships.

Helping Shy Men is Our Specialty

October 7, 2016

There are many different personality types in the dating world. Some men are naturally outgoing, while others are more reserved, thoughtful, and introspective. Over the…

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Asian couple enjoying a warm conversation during a romantic dinner date in an elegant restaurant.

When Is It Okay to Ask Him Out?

October 5, 2016

Many women ask me this question privately:“Is it okay for me to ask him out?” And just as important:“When is the right time to do…

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How Men Can Be Better Daters

May 5, 2016

Over the years, I’ve had the privilege of working with many accomplished, thoughtful men who are genuinely ready to find a meaningful relationship. They come…

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Professional man in a modern, softly lit living space speaking on the phone with a relaxed and confident expression, representing intentional and personal communication in dating

Los Angeles Dating Tip: Call Her

April 29, 2016

One of the simplest ways to set yourself apart in today’s dating landscape is also one of the most overlooked. Call her. In a culture…

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Elegant couple on a refined dinner date, sharing a warm, intimate moment in a softly lit restaurant setting, representing meaningful cross-cultural connection and intentional matchmaking

Jewish Man Asian Woman Connections

April 29, 2016

A Closer Look at Cross-Cultural Compatibility   In recent years, I’ve been asked more frequently about the dynamic between Jewish men and Asian women. It’s…

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Asian Dating Tip or Two

April 29, 2016

Asian Dating Tip #1: “I can’t afford an Asian matchmaker. What are my other options?” I hear this question more often than you might expect.…

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Asian woman and Western man enjoying a relaxed, elegant conversation over coffee in a softly lit setting, reflecting connection, shared values, and intentional dating

Asian Women Find These 2 Things Very Important

April 29, 2016

When I speak with clients about dating Asian women, one question comes up often: What truly matters to them? While every individual is different, there…

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Asian Men Dating Outside Of Their Race

March 30, 2016

Asian Men are educated, intelligent, and family-oriented Over the years, I’ve worked with many Asian men who are open to dating outside of their race.…

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When You Hire An Asian Matchmaker

May 7, 2015

When you choose to work with an Asian matchmaker, the experience is often more than you expect. It’s not simply about meeting someone new. It’s…

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Warm editorial-style portrait of Matchmaker May in a calm indoor setting, reflecting thoughtful relationship guidance, emotional readiness, and intentional modern dating.

Dating Expert Says You Are Not Ready To Date If…

May 5, 2015

When I speak with newly single clients, one of the first things I often say is this: You do not need to rush back into…

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