Why Your Marriage Should Start With a Bold Choice: The Story of Sarah, Rafi, and Breaking Free From "What You're Supposed to Do"By Cantor Ben Silverberg

Why Your Marriage Should Start With a Bold Choice: The Story of Sarah, Rafi, and Breaking Free From "What You're Supposed to Do"

By Cantor Ben Silverberg

You’ve been lied to.

I was lied to.

At 16 years old, I sat across from a well-meaning teacher who looked me in the eye and said:

“Become a doctor, a lawyer, or an accountant. Otherwise, no woman will feel safe marrying you. You won’t be able to support a family.”

When I asked, “What about entrepreneurship? What about building something meaningful and different?”

She shut it down.

“That’s not for you. Be realistic. Stop dreaming.”

I walked out of that conversation carrying a heavy truth: if I had listened, I would have spent the rest of my life chasing someone else’s idea of success—and not my own.

But I didn’t listen.

Instead, I created a global online Hebrew school. I’ve helped hundreds of kids prepare for their Bar and Bat Mitzvahs and grow into confident, courageous young adults. I’ve stood under the Jewish Wedding Chuppah with couples like Sarah and Rafi in beautiful Jewish Wedding Ceremonies across Toronto, guiding them as they begin the most meaningful chapter of their lives.

And what I’ve learned along the way is this:

Marriage isn’t about doing what you’re “supposed to do.”

It’s about choosing what’s right for you. Boldly. Bravely. Unapologetically.

Sarah and Rafi: Choosing Tradition—and Innovation

When Sarah and Rafi first contacted me about officiating their Jewish Wedding Ceremony in Toronto, they were excited—but they were also feeling pressure.

Not just from the logistics of Jewish Wedding Planning—choosing a Jewish Wedding Venue, picking the right Jewish Wedding Music, coordinating with the Jewish Wedding Photographer, and designing Jewish Wedding Invitations.

They were also feeling pressure to fit a mold.

Both came from loving, traditional families. But they didn’t want a carbon copy of their parents’ wedding. They wanted something meaningful. Personal. Rooted in Jewish Wedding Traditions but reflective of the life they were building together.

They wanted a Jewish Wedding Cantor who would celebrate their individuality while still honoring sacred Jewish Wedding Customs—like the Jewish Wedding Ketubah, the Jewish Wedding Vows, and yes, of course, the epic Jewish Wedding Hora!

Together, we created a wedding experience that blended Modern Jewish Wedding style with Traditional Jewish Wedding Rituals, resulting in one of the most powerful and personal Jewish Wedding Celebrations I’ve ever had the honor of leading.

They didn’t settle.

They made a decision.

They chose them.

And I believe that’s where every great marriage begins.

Marriage Is a Covenant of Courage

Too often, couples feel obligated to do things "the way it’s always been done"—even if it doesn’t feel like them. From the Jewish Wedding Attire to the Jewish Wedding Decorations, it’s easy to fall into the trap of comparison, performance, and expectation.

But the most extraordinary weddings I’ve officiated—like Sarah and Rafi’s—are never about perfect details. They’re about the courage to say:

“This is who we are. This is the kind of marriage we want to build. And this is how we’ll begin.”

As someone mentored by a great Jewish wedding Rabbi, I’ve learned that our traditions were never meant to confine us—they’re meant to guide us. To root us. To give us the strength to make bold choices with a sacred foundation.

The Lesson Behind the Chuppah

The Jewish Wedding Chuppah isn’t just a canopy. It’s a powerful symbol.

It says: “This is our sacred space. This is where our story begins.”

It doesn’t have to look like your cousin’s. Or your grandmother’s.

It just has to hold you.

Sarah and Rafi chose a Jewish Wedding Officiant who would speak about their values, their dreams, their love for Jewish tradition—and their love for creativity.

Their ceremony included heartfelt readings, personalized reflections, and traditional blessings. But it also included laughter, vulnerability, and a message that hit every guest in the heart:

You don’t have to follow the script.

You just have to follow your values.

The Ripple Effect of One Bold Decision

Here’s what most people don’t realize:

Every bold choice you make—every time you say yes to what feels right and no to what doesn’t—sets off a ripple effect.

Sarah and Rafi didn’t just create a stunning Jewish Wedding Toronto moment.

They created a model. A message to their future children, their friends, and their community that said:

“You don’t have to play small. You were made for a time different from your parents’. And you deserve to build a life that honors that.”

Since their wedding, I’ve been honored to stay in touch with Sarah and Rafi. They’ve already talked about bringing me back for their future Jewish Baby Naming Ceremony and involving me in their Jewish Newborn Ceremony—when that time comes.

That’s the power of a bold beginning. It builds a life filled with intentionality, celebration, and joy.

Final Thought: What Will Your Wedding Say About You?

You can have a Jewish Wedding Celebration that checks all the boxes…

Or you can have a Jewish wedding that tells your truth.

One that weaves in everything you love about Jewish Wedding Traditions—the Ketubah, the Hora, the Jewish Wedding Dance—but in a way that feels authentic to your relationship.

As a Jewish Wedding Cantor, I don’t just guide ceremonies.

I help couples find their voice.

And that begins with a decision—to lead your marriage the same way I teach students to live:

Boldly.

Joyfully.

And fully aligned with your truth.

Ready to begin your Jewish wedding journey in a way that reflects the real you?

Let’s connect. I’ll help you plan a ceremony that honors both where you come from and where you’re going—with warmth, meaning, and purpose.

Because your wedding should be more than beautiful—it should be yours.

[Reach out today to start planning your Jewish Wedding in Toronto.]