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Let's connect An Eight-Week Journey in Supporting Singles with Clarity, Care, and Confidence
For matchmakers who want to bring greater understanding, intention, and wisdom to the work they already care so deeply about.
Register for the Course →A different approach
What if we could approach difficult moments with greater understanding—not only of the singles we’re working with, but also of ourselves and the role we play in their lives?
Shadchanus with Heart & Wisdom is an eight-week learning experience designed to help matchmakers develop a more grounded, thoughtful, and relational approach to their work.
Together, we’ll explore how to support singles with care and sensitivity, offer guidance without taking over, and remain wholeheartedly involved while recognizing what is—and isn’t—ours to carry.
The learning
Throughout the course, we’ll look at questions such as:
Our learning will include reflection, practical examples, group discussion, and opportunities to apply what we’re learning to real matchmaking situations.
The goal isn’t to become a perfect matchmaker or to have an answer for every situation.
It’s to become more grounded in your role, more skilled in how you listen and guide, and more confident about when to step in and when to step back. It’s about learning how to help singles move forward, even when everything isn’t perfectly clear, while respecting their pace, their choices, and their ability to find their own way.
Why it matters
Shadchanim are invited into one of the most personal and emotionally sensitive areas of a person’s life. And yet that sensitivity isn’t always obvious.
The singles we work with may be successful, capable, accomplished people who seem to manage so many other parts of their lives beautifully. That can make it even more confusing when dating brings out uncertainty, fear, indecision, frustration, or reactions that simply don’t make sense to us.
But what we’re seeing may only be the tip of the iceberg.
Dating can touch incredibly tender places—hope, rejection, self-worth, vulnerability, the longing to build a life, and the reality that so much of what someone desperately wants is outside of their control.
People don’t come to us wearing a sign that says:
And that gives the role of a shadchan real emotional weight.
With the best of intentions, we can inadvertently add to someone’s pain when we don’t understand the sensitivity of what is happening beneath the surface.
But the opposite is also true. With strong relational skills, a shadchan can do a world of good.
We can learn to listen differently. To become curious rather than assume. To recognize when to encourage and when to give someone room. To bring compassion and generosity of spirit to reactions we may not fully understand.
We don’t need to become therapists. But we do need the relational skills to meet people with greater understanding during what may be one of the most vulnerable periods of their lives.
Course experience
90 minutes each, with time to learn and reflect together.
Space for learning, reflection, and applying the material to your own experiences.
Thoughtful reminders, occasional videos, mini-quizzes, and practical exercises throughout the week.
Available if you miss a session or want to revisit the material.
Opportunities to reflect, share experiences, and learn alongside other matchmakers.
Practical examples and opportunities to apply what you learn to your own work.
Join us
Begins Monday, October 26, 2026
Mondays, 2:00–3:30 PM Eastern
Eight weekly live Zoom sessions
Recordings included
Occasional schedule adjustments may be needed.
What you can bring back to your work
The aim is not to have an answer for every situation, but to build skills you can use in the moments that matter.
A personal invitation
Having worked in Shadchanus and with singles for over twenty years—and becoming a trained psychotherapist along the way—I’ve seen both how much heart matchmakers bring to this work and how complicated the role can become.
We care deeply. We see possibilities. We want to help.
And through my work with singles, I’ve also had the opportunity to understand more of what their dating experiences can feel like from the inside—how much may be happening beneath the surface, even when it isn’t obvious to those trying to help.
Over the years, I’ve come to appreciate just how much our way of showing up matters.
That’s why I created Shadchanus with Heart & Wisdom.
I wanted to bring together what I’ve learned from both worlds and create a place where we could look more deeply at the work behind the work of Shadchanus—how we listen, how we guide, what happens inside us when we care deeply, and how we can use the influence we have with greater wisdom and care.
My hope is that this course gives you not only new ideas, but practical relational skills that become part of how you work—helping you feel more grounded and helping the singles you work with feel more understood, respected, and supported.
I look forward to learning together.
Ilana Brown
Registered Psychotherapist | Relationship & Dating Coach