Wedding Lessons: What Melissa and Adam Taught Me About Taking the Shot (and Why It Matters for Life)

If you think trying is risky, wait till they hand you the bill for not trying.

It’s a line I say often—because I’ve lived it, I’ve seen it, and I’ve coached others through it. Trying is uncomfortable, vulnerable, and yes, sometimes it hurts. But you know what hurts more? Regret.

I had a student once who was terrified to audition for her school’s musical. She was maybe 12, sweet and bright, but stuck. When I asked why she didn’t want to try, she told me something heartbreaking: “My uncle told me five years ago that I can’t sing. I’ve been afraid to try ever since.”

That’s how fear gets planted. A single sentence, a single moment—and suddenly, a child’s light dims.

But here’s the truth: trying isn’t about winning. It’s about refusing to let fear write your story.

Melissa and Adam’s Wedding: A Love Story Fueled by Courage

I was reminded of this powerful lesson when I officiated the Jewish Wedding Ceremony of Melissa and Adam in Toronto. When they came to me to lead their Jewish Wedding Toronto celebration, I saw immediately that they were something special. Not just because of their love—but because of their story.

Adam, like many grooms, was initially nervous about speaking publicly during the ceremony. Melissa had been dreaming of saying personalized Jewish Wedding Vows under the Jewish Wedding Chuppah, but Adam hesitated. He told me, “Ben, I’m not a good speaker—I don’t want to mess this up in front of everyone.”

But I reminded him: “If you don’t try, you’ve already lost. This moment isn’t about perfection. It’s about presence. About showing up fully for Melissa.”

And he did. He took the shot. He wrote beautiful, heartfelt vows that brought everyone—myself included—to tears. That moment became one of the most unforgettable parts of their Jewish Wedding Celebrations.

When I asked them afterward what they were most proud of from the day, Melissa said: “The fact that we showed up for each other. We didn’t hide. We didn’t shrink. We leaned in.”

And that’s the real essence of love—and leadership. Showing up.

Break It Down: Trying Isn’t the Risk. Not Trying Is.

The reason most people don’t try isn’t because they’re lazy. It’s because they’re scared. They’ve attached their identity to outcomes. If I win, I’m worthy. If I fail, I’m broken.

But that’s not how growth works.

Trying is about courage. It’s about training your brain to value effort over ego. It’s the mindset that says, “Even if I fall, I’m stronger for having tried.”

In my CoolCantor program, I teach this principle not only to teens preparing for their Bar Mitzvah or Bat Mitzvah, but also to adults. That’s right—Adult Bar Mitzvah and Adult Bat Mitzvah students come to me often saying, “I should’ve done this years ago, but I didn’t think I could.”

And I tell them the same thing I told Melissa and Adam: It’s never too late. The decision to try now is what builds your legacy.

How This Ties Into Jewish Wisdom

In Judaism, we don’t celebrate people for being perfect. We celebrate them for trying, for showing up, for wrestling with challenge. Look at Moses—he doubted himself every step of the way. “I’m not a good speaker,” he said to God. But he still took the mission.

Leadership, confidence, and resilience all begin with a single decision: I’m willing to try.

That’s what I teach in all my Judaism Classes Online, whether it’s Online Bar Mitzvah Lessons, Online Bat Mitzvah Training, or even Virtual Bar Mitzvah Lessons. Every lesson I create is grounded in that belief—that growth comes from movement, not mastery.

Jewish Weddings Are Life Lessons in Disguise

A Traditional Jewish Wedding is full of Jewish Wedding Rituals that teach this same lesson.

The Jewish Wedding Ketubah? It’s a declaration to try. To commit.

The Jewish Wedding Dance, the Jewish Wedding Hora? Celebrations of two people showing up, surrounded by those lifting them up.

Even the act of breaking the glass is a metaphor—yes, the world is imperfect, and yes, we’ll still try to build something beautiful within it.

Melissa and Adam’s Jewish Wedding Officiant experience was filled with these moments. They carefully selected Jewish Wedding Music, personalized their Jewish Wedding Invitations, and planned a Jewish Wedding Reception that reflected their values. From their Jewish Wedding Venue to the Jewish Wedding Photographer they chose—it was a celebration of trying, creating, and leading with love.

And they didn’t stop there. Months later, I received an email from them asking me to officiate their upcoming Jewish Baby Naming Ceremony. Yes, they were already thinking about building a legacy.

From Jewish Baby Naming Services to Jewish Baby Naming Tradition, I help families celebrate these milestones. Whether it’s a Jewish Newborn Ceremony or Baby Naming Ceremony Jewish-style, I provide guidance, meaning, and joy—because every ritual is a chance to show up.

Final Thought: Will You Let Fear Decide?

What Melissa and Adam—and that student afraid to sing—taught me is this:

Trying doesn’t guarantee success. But not trying guarantees regret.

If you’re planning your wedding, your child’s Bar or Bat Mitzvah, or a Jewish Baby Naming Ceremony, don’t let fear run the show. Let courage speak. Let love lead.

As a Jewish Wedding Cantor—mentored by a great Jewish Wedding Rabbi—I bring deep tradition, real-world inspiration, and modern warmth to every ceremony I officiate.

And if you’re ready to make your event more than just a moment—but a memory that builds confidence, community, and courage—let’s talk.