What if finding love was less about swiping and more about living intentionally? In this fascinating conversation, May sits down with Rebeccah Lipson, a Boston-based Jewish matchmaker with a refreshingly real take on modern romance.
Forget the endless checklist — Rebeccah breaks down why your lifestyle, your values, and even the relationship you watched your parents model matter far more than any dating app algorithm ever could.
From the surprising similarities between Jewish and Asian dating culture, to the power of showing up in your community (yes, synagogues and volunteer events still work!), this episode is packed with insights that will genuinely shift how you think about love.
Whether you're actively dating or just love a great conversation about human connection, Rebeccah's best dating tip alone is worth the watch.Hit play — your future self might thank you. 0:00 Introduction to Boston Matchmaker who happens to be Jewish: Rebeccah Lipson3:12 Soulmate is who you marry5:20 Should you have a checklist8:00 Your lifestyle really matters14:00 Your role model parents17:09 Pitch a friend organization23:50 Don’t rely on apps for dates, try volunteering & synagogues28:05 Jewish men and Asian women similarities30:30 Convert into Judaism35:27 Rebeccah’s best dating tipRebeccah Lipson is the founder of Connection Club, a Boston-based matchmaking service for serious singles ready to find a long-term partner. With hundreds of singles interviewed, she's developed a sharp instinct for what creates lasting, meaningful chemistry. She believes love is the most significant force in life — and she's built her work around delivering that sense of epic connection to her clients.Rebeccah is a proud member of the Matchmakers Alliance, a network of experienced matchmakers and dating coaches. She also serves as the Boston City Organizer of Pitch a Friend — a unique event where friends reserve a spot to deliver a 3–5 minute slide presentation making the case for why their person is an incredible catch, covering their best qualities, fun facts, and what they're looking for in a relationship.https://www.connectionclubmatchmaking.com/*AMAZON BEST SELLER* Get my book, ‘A Roadmap For Single Asian Women’ here: https://www.amazon.com/dp/B0C9L4CT87?ref_=cm_sw_r_cp_ud_dp_FKWJGPCVXW3XG8D98EWB Call May for help: (310) 867-0851Join The Best Asian Matchmaker’s Database Here: https://www.twoasianmatchmakers.com/profileEmail: [email protected]: www.twoasianmatchmakers.comFacebook Page: https://www.facebook.com/TwoAsianMatchmakersInstagram: https://www.instagram.com/matchmakermayTiktok: https://www.tiktok.com/@asianmatchmaker88LinkedIn: https://www.linkedin.com/in/mayhui/ABOUT THIS PODCAST: THE ASIAN DATING PODCASTWhat does Matchmaker May Do?You know how high-net-worth men are accomplished in their careers but too busy to date? They value time more than money, yet struggle to find meaningful connection. What I do is learn who they want to attract, screen the women for them, and make the introductions—so instead of wasting time, they meet the right woman and fall in love.May talks about all things dating and Asian dating. She’s super nosy about people’s love lives and just loves love. May is a Professional Matchmaker and Dating Coach. May is the founder of Two Asian Matchmakers, a boutique matchmaking agency. Since 2009, May has helped successful men who appreciate Asian culture and value meaningful connection find their ideal Asian partner in the United States and Asia.May is a highly respected and active member of the Matchmakers Alliance and Global Love Institute in New York. May’s insights and work have been featured in major media outlets including Cosmopolitan, Los Angeles Magazine, Thrillist, and Huffington Post, establishing her as a go-to expert in love, dating, and human connection.