Inside May Bugenhagen’s Approach to Matchmaking: Where Personal Connection and Cultural Understanding Shape Outcomes
Apr 17, 2026
The entry of May Bugenhagen, founder of Two Asian Matchmakers, into matchmaking began as a response to a personal realization about the gaps in modern dating. From her perspective, navigating relationships while maintaining a stable career and fulfilling personal life revealed a disconnect between
opportunity and meaningful connection. That experience led her to examine how people meet and why, despite an abundance of options, many still struggle to form lasting relationships.
When May Bugenhagen began her career, matchmaking was not part of the plan. According to her, the idea took shape through personal experience, after navigating her own challenges with dating despite having what she describes as a stable career and fulfilling personal life. That moment, she explains, prompted a broader question about how people connect in a world where opportunities to meet are abundant but often ineffective.
“I remember thinking that I had done everything right, from building a career to creating a good life, and yet I still struggled to find the right person,” Bugenhagen says. “That made me realize there was space for something more thoughtful and more intentional in how people meet.”
May Bugenhagen
From that realization, she founded Two Asian Matchmakers, a boutique matchmaking service that works primarily with men seeking long-term relationships with Asian women. “It operates as a personalized service rather than a digital platform, focusing on direct interaction, screening, and guided introductions,” she says.
Her approach is shaped by both lived experience and professional observation. Having spent years learning about relationships through books, conversations, and personal reflection, Bugenhagen notes that dating is often treated as something people are expected to navigate without guidance. That gap, she explains, continues to influence how she structures her work today.
“I became interested in understanding how people meet, what makes relationships work, and why certain patterns repeat,” she says. “Over time, that curiosity turned into something I wanted to build professionally.”
The model she developed reflects that intention. Instead of relying on algorithms, Bugenhagen explains that she personally vets candidates, conducts interviews, and facilitates introductions. According to her, this process allows for a deeper understanding of compatibility beyond surface-level preferences.
She frames the workflow as highly structured yet flexible. Clients are onboarded through interviews and questionnaires, followed by curated introductions that are arranged only after both parties express interest. “My role is to understand what each person is really looking for and then create opportunities that align with that,” she says. “It’s about making the process more focused and more personalized.”
Bugenhagen also emphasizes the importance of communication and accountability within her network. From her perspective, how individuals engage throughout the process is as important as their stated preferences. She explains that reliability, responsiveness, and mutual respect are key factors she considers when evaluating potential matches.
Beyond the matchmaking process itself, Bugenhagen integrates her insights into a podcast, The Asian Dating Podcast, that explores dating from multiple perspectives. She notes that the platform allows her to engage with different viewpoints while continuing to refine her understanding of how relationships evolve over time.
“The goal is to keep learning,” she says. “Dating is always changing, and hearing different perspectives helps me stay informed and bring that knowledge back to my clients.”
She explains that her client base is highly selective. Rather than working with a high volume of individuals, Bugenhagen focuses on maintaining a smaller portfolio, which allows her to dedicate more time and attention to each case. According to her, this approach supports a more personalized experience and enables her to remain closely involved throughout the process.
Looking ahead, Bugenhagen sees matchmaking continuing to evolve alongside broader cultural and technological shifts. She notes that while digital tools have expanded access, they have also introduced new complexities that require a more guided approach. In response, she plans to continue refining her model while expanding her reach into new regions.
“In the coming years, I’d love to see a renewed emphasis on genuine, in-person connection, people taking the time to meet, engage, and build relationships beyond the screen,” she says. “There’s something powerful about shared, real-world experiences that I think is worth bringing back.”
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