Ask For More: Lessons From A Jewish Wedding in Toronto

Hi, I’m Cantor Ben. I was mentored by a great Jewish

wedding Rabbi, and though I am not a Rabbi myself, I’ve carried forward

his wisdom into my work as a Jewish Wedding Cantor and officiant. Over

the years, I’ve had the honor of standing under countless chuppahs,

guiding couples through one of the most sacred moments of their lives.

Each ceremony isn’t just about vows and rituals—it’s about values. And

the values we live out on our wedding day often shape the homes,

families, and legacies we build afterward.

Let me tell you a story about Mandy and Josh, a beautiful

Jewish couple from Toronto, whose wedding I had the privilege of

officiating. Their story illustrates one of the most important lessons I

share with both couples and students alike: don’t play small—ask for

more.

The Power of Asking

They told you not to ask for too much. “Be grateful for

what you have. Don’t expect more.” But history is full of people who

challenged that mindset.

Take the woman from Spanish Harlem who grew up in poverty.

She had an idea for an umbrella that lights up when you open it. That

one invention grew into a business worth over $300 million a year. She

now sits on the board of Office Depot. Why? Because she asked. She

believed she was allowed to dream bigger and expect more.

Mandy and Josh embraced that same spirit when planning

their Jewish Wedding in Toronto. They didn’t settle for just going

through the motions. They asked: “How can we make this not only a

celebration but also a statement of who we are and the family we want to

build?”

That question changed everything.

Jewish Wedding Services That Reflect Values

For their Jewish Wedding Ceremony, Mandy and Josh wanted a

balance of Traditional Jewish Weddings and elements of Modern Jewish

Weddings. They wanted the sacredness of Jewish Wedding Rituals—the

signing of the Jewish Wedding Ketubah, the blessing under the Jewish

Wedding Chuppah, and the joyful Jewish Wedding Hora—but also touches

that reflected their modern love story.

During Jewish Wedding Planning, we talked about the

symbolism of each moment. The chuppah wasn’t just a canopy; it

represented the home they would build together. The ketubah wasn’t just a

document; it was a covenant of values. And the hora wasn’t just a

dance; it was a joyful reminder that love lifts us higher when we’re

surrounded by family and friends.

By asking more of their ceremony—not just “How do we

follow the customs?” but “How do we weave meaning into them?”—they

created a day that their guests still talk about.

Beyond the Ceremony: Building a Legacy

One of my favorite parts of working as a Jewish Wedding

Officiant is staying in touch with couples long after the wedding. For

Mandy and Josh, the journey didn’t stop after their Jewish Wedding

Reception. When they welcomed their first child, they reached out again

for a baby naming ceremony Jewish families hold so dear.

Just like their wedding, they didn’t want the Jewish Baby

Naming Ceremony to be a formality. They wanted it to be a true Jewish

Baby Naming Celebration, a moment that connected their child to

generations of Jewish tradition. Together, we planned a Jewish newborn

ceremony filled with blessings, music, and personalized prayers. We even

talked about future milestones—education, mitzvah projects, and how to

raise a child who dreams bigger than the world tells them to.

Jewish Wisdom On Asking For More

Judaism has always taught us that asking is holy. Abraham

asked God questions. Moses asked for courage. Esther asked for the lives

of her people. To ask is not to be ungrateful—it is to be alive to

possibility.

The Torah reminds us that our words create worlds. When we

raise children to believe they can ask for more—to request guidance, to

pursue opportunity, to seek justice—we prepare them to lead. When we

silence that voice, we risk raising adults who play small, even when

greatness is within reach.

A Life Coaching Perspective

As a Cantor and Life Coach, I often see entitlement on one

side and fear of asking on the other. Entitlement says, “I deserve this

without effort.” Fear says, “I’ll never get it, so why try?”

But true confidence lives in the middle. It says, “I am

willing to ask, to try, to persist—and I will honor the opportunities

that come my way.”

This is exactly what I train young people to practice.

Whether through Torah study, mitzvah projects, or even simple

conversations, I remind them: confidence isn’t a gift, it’s built. And

one of the bricks is learning to ask boldly.

Lessons From a Jewish Wedding in Toronto

When I think back on Mandy and Josh’s wedding, I don’t

just remember the flowers or the music, though their Jewish Wedding

Music and Jewish Wedding Decorations were truly stunning. I remember

their intentionality.

They chose a Jewish Wedding Venue that symbolized openness

and light. Their Jewish Wedding Photographer captured candid moments of

laughter, not just posed smiles. Their Jewish Wedding Invitations

included a blessing that spoke of gratitude and abundance. Their Jewish

Wedding Attire reflected respect for tradition while embracing modern

style. Every detail, from the Jewish Wedding Vows they exchanged to the

way they danced at the hora, said the same thing: We are not afraid to

ask for more from life and love.

And that is why their Jewish Wedding Celebrations were so powerful.

Your Challenge This Week

Here are three ways you can take this lesson home:

1. Model Asking: The next time you’re at a restaurant or event, let your

child see you politely ask for what you need—a seat change, a meal

adjustment, or a moment of clarification.

2. Dream Bigger as a Family: Write down one dream you’ve been holding back on because it feels “too big.” Share it out loud with each other.

3. Revisit Tradition With Intention: Whether it is a holiday meal or a family

blessing, don’t just go through the motions. Ask, “How can we make this

more meaningful?”

Final Thought

They told you not to ask for too much. But the truth is,

asking is how we honor life’s potential. Mandy and Josh’s Jewish Wedding

in Toronto reminded me of that. They turned their Jewish Wedding

Ceremony into a living expression of courage, generosity, and faith.

They embraced Jewish Wedding Customs with creativity, and they planted

seeds for a future filled with love and legacy.

If you are planning a wedding, a Jewish Baby Naming

Ceremony, or exploring ways to celebrate Jewish life with intention,

remember this: you are allowed to want more. In fact, our tradition

encourages it.

Ask. Receive. Build something lasting.

Thanks,

Ben