Rolling With the Punches: A Last-Minute Musical Havdalah Adventure with cTeen

You know that feeling when life throws you a complete curveball, and you've got about thirty seconds to decide if you're gonna swing or duck? That was me this past Shabbos, and let me tell you – sometimes the best adventures happen when you least expect them.

So there I was, Thursday afternoon, minding my own business when my phone buzzes. It's my friend, one of the Rabbis from cTeen Tristate. "Hey Tali, any chance you could do a musical Havdalah this Saturday night? We're having a Shabbaton, and after Shabbos ends, we're taking the kids to American Dream mall, then Nickelodeon."

American Dream mall for a musical Havdalah? Now that's something you don't hear every day. But hey, I'm always down to share some music with Jewish teens, so I said yes without thinking twice.

Fast forward to Friday afternoon – a few hours before Shabbos. Phone rings again. Plans have changed. No more American Dream mall. They're doing the Havdalah right at Chabad of Tenafly where the Shabbaton's happening. Cool, I can roll with that.

Then comes the real kicker.

"Oh, and Tali? Our guest speaker's flight just got cancelled. Think you could fill in? You'd need to spend Shabbos here in Tenafly."

Now, any married guy reading this knows what happened next. I did what any smart Jewish husband would do – I asked my wife. And bless her heart, she took one look at the situation and said, "Pack the car."

What followed was pure chaos. My wife, being the absolute champion that she is, quickly packed up all our Shabbos food into the fridge and freezer, then started throwing clothes and kid stuff into bags for us and our two little ones. We're talking full family relocation mode in under two hours.

"Hashem guides the steps of man," goes the morning blessing. Sometimes those steps are more like a full sprint to the car with your guitar in one hand and a diaper bag in the other.

We literally pulled up to the Clinton Inn just as the teens were gathering to light Shabbos candles about 30 minutes before Shabbos (they were taking it on a little bit earlier). I'm talking movie-timing here – couldn't have cut it closer if we tried. One of the staff helped my wife get our stuff to the room while I grabbed my guitar and headed straight to the hall where everyone was waiting.

Pre-Shabbos concert time.

There's something special about that moment right before Shabbos kicks in. The energy, the anticipation – it's electric. I looked out at this room full of Jewish teens from all different backgrounds, all different stories, and I knew exactly what I wanted to talk about.

Jewish continuity. The unbreakable link between our people and the Holy Land. But most importantly, how it's up to us – every single one of us – to make sure we're not the last Jews in our family line.

We dove right into my father's #1 hit song 'My Zaidy'. You should've seen these kids' faces light up as we sang together. There's something about that song that just hits different – three generations of Jewish experience wrapped up in melody and memory.

But then we closed with "Tamid Ohev Oti" – originally composed by Yair Elitzur, popularized by Sasson Ifram Shaulov. For those who don't know, it means "Always Loves Me," and since the Gaza war, it's become this unofficial anthem in Israel talking about how no matter who we are or where we're holding in life, "Hashem Always Loves Me".

Let me tell you something – that song got everyone HYPE. Despite all their different backgrounds, different levels of observance, different everything – they all sang it loud and proud. Music really is the ultimate uniter of people. In that moment, we weren't just teens and adults in a hotel conference room. We were Jews, connected by something deeper than words.

Shabbos itself was incredible. I got to speak to the kids twice, and both times blew my mind with how engaged they were.

The first speech was about the soul's journey. I opened by asking who plays video games – not surprisingly, most hands shot up. I named a few games I've played with my own teens, and suddenly I had their complete attention.

"What happens when you stop moving the joystick?" I asked.

"The character stops moving, duh!" they all said.

"Exactly. You animate that character the same way your soul animates your body. On Shabbat, we feel like physical beings having a spiritual experience, but really? We're spiritual beings having a physical experience down here."

I called it "Are We Living in a Simulation?" – trending topic on social media, ancient Jewish wisdom. Same concept, different package.

The second speech hit even closer to home. I talked about being a Jew first, everything else second. That's how the secular world has always seen us anyway – might as well wear it with pride instead of shame.

Then I gave them an a cappella preview of a song from my upcoming album, Holy Outlaws Volume 2. It's called "I'm a Jewish American, Not an American Jew." The distinction matters more than people realize.

By the end of Shabbos, these teens had experienced something most of their generation rarely gets – twenty-four hours completely unplugged. No phones, no social media, just genuine human connection. They played games, did sports, and here's the kicker – they visited nursing homes to spend time with elderly folks who don't get many visitors.

That act of Chesed? That kindness? That's the stuff that really matters. Those kids definitely scored some serious brownie points with Hashem that day.

But the Musical Havdalah – oh man, that was the stuff of legends.

Picture this: dozens of Jewish teens, voices raised in unison and harmony, marking the end of Shabbos with music that filled every corner of that space. The whole group jumped in on the melodic chorus, singing in perfect unison. It wasn't just a ceremony – it was pure celebration.

After Havdalah, we did a medley of upbeat Jewish songs before they headed off to American Dream for their Nickelodeon adventure. Watching them pile into those buses, still buzzing with energy from our musical send-off, was something else.

The whole event turned out to be this incredible success, but here's what really gets me – none of it was planned. There's this old Yiddish expression: "A Mentch Tracht, Un Got Lacht." Loosely translated, it means "A man plans, and God laughs."

I thought I was going to have a nice, low-key Shabbos at home with my better half. Turns out our Creator had totally different plans for us. And you know what? I'm glad we were able to step up for such a special organization that's doing everything possible to enrich our most precious investments – our kids – with Jewish and Torah values.

Sometimes the best adventures happen when you're least prepared for them. Sometimes saying yes to the unexpected leads to exactly where you're supposed to be.

Ready for your own musical adventure? Whether it's a last-minute Shabbaton or a planned community event, I'm here to bring authentic Jewish music to your organization. Check out my booking page and let's create something meaningful together.

Until next time – keep rolling with those punches. You never know where they might lead you.