What 1,000 Weddings Taught Me About Planning My Perfect Wedding
- Erika Van Pelt
- 4 hours ago
- 9 min read
Here’s what 20 years in the wedding industry taught me about planning a wedding.
I sang my very first wedding ceremony at my church when I was seven years old.
At 19, I joined my first wedding band. I flew in a tiny puddle-jumper airplane to Nantucket during a storm to perform at my very first wedding reception. I’ve performed in grand ballrooms, on beaches, in vineyards, and in tiny historic churches - even the American Idol stage (more on that later)!
For the last 21 years, I’ve performed 40–50 weddings every year as a singer, bandleader, and DJ.
And somewhere along the way, I crossed the 1,000 wedding mark.
Besides making me feel a little old (ha!), that milestone was honestly a moment of simultaneous shock and gratitude. Being invited into such an important day in the lives of so many couples is incredibly special. Singing someone down the aisle or DJing the moment their entire dance floor erupts — those are moments I never take for granted.
But after witnessing more than a thousand weddings, I definitely thought:
I already know how this works.
Then I started planning my own wedding.
And suddenly, I saw everything from a completely different perspective.
Planning my wedding taught me lessons I never expected - about emotions, priorities, family dynamics, and what truly makes a wedding memorable.
If you’re planning your wedding right now, here are a few things I’ve learned from both sides of the experience.
Understanding the Emotional Landscape of Weddings
Weddings are emotional.
I knew that from performing at them for two decades, but planning my own made me realize just how intense those emotions can be.
Over the years I’ve witnessed countless powerful moments - couples sobbing during their vows, parents and family members beaming with pride, entire dance floors singing and screaming together at the top of their lungs...
But the moments that stick with me the most are always the deeply personal ones.
One wedding I’ll never forget happened in a small church where I was singing a duet with one of my bandmates. During the bride’s processional, two ballet dancers performed a choreographed duet on the altar while we sang.
It was incredibly beautiful and deeply personal - and the entire room could feel it.
Those are the moments that make weddings unforgettable.
Planning my own wedding also made me realize something I hadn’t fully appreciated before: how many decisions carry emotional weight.
Even something like who will walk you down the aisle can suddenly feel incredibly important when you’re thinking about family dynamics.
Let's face it - it can be really overwhelming.
Acknowledging that emotional landscape - instead of trying to ignore it - makes the planning process much easier to navigate.
The Power of Personalizing Your Wedding
After performing at over 1,000 weddings, I can confidently say this:
The weddings that feel the most memorable are the ones that feel personal.
Generic weddings tend to have a few things in common:
cookie-cutter playlists
rigid timelines
rushing through the formalities
On the other hand, the weddings that stand out are the ones where couples take the time to create intentional moments.
For our wedding, we wanted to lean all the way into that idea.
Instead of hiring a traditional officiant, we asked one of our musician friends to officiate the ceremony.
My husband walked down the aisle to a spoken monologue from My Fair Lady , channeling his inner Rex Harrison - instead of a song. It made everyone laugh and instantly relaxed the entire atmosphere.
For my parent dance, I chose to dance with my mom, which was a very personal decision for me.
And because we both come from Irish families, we hired a mobile Irish pub to pour Guinness throughout the reception.
Inside the pub, we had traditional Irish musicians playing live.
But the biggest personal element of all?
Because we’re both musicians, we didn’t hire a band or DJ. Instead, one of our vendor friends graciously brought in sound and lighting, some guests brought backline PA equipment in, and we hosted a massive jam session with over 60 musicians in attendance.
The result was something completely unique to us.
And that’s the goal.
Why Clear Communication Matters So Much
After seeing hundreds of weddings unfold behind the scenes, I can tell you that miscommunication is one of the biggest causes of stress on a wedding day.
One common example is timelines.
Often the planner or catering manager creates the timeline - but music flow isn’t always part of that conversation. When timelines don’t account for how the energy of the room actually works, it can really impact the overall experience.
I’ve also seen situations where information simply didn’t make its way to the right people.
At one wedding years ago while I was working for an agency band, the administrative team forgot to tell the band that the couple wanted their first dance performed live.
Unfortunately, none of us had learned the song.
That led to one of the most stressful conversations of my career, where I had to apologize to the bride and ask whether she’d prefer us to play the recorded track or perform a different song live.
Thankfully she chose the live option and ended up loving it - but it was a perfect example of how important communication is.
Planning my own wedding made me realize why vendors ask so many questions.
Ironically, the more relaxed you want your wedding to feel, the more planning details you have to clarify in advance.
Managing Expectations and Staying Flexible
One thing I learned after 1,000 weddings is that something unexpected always happens.
And that’s okay.
At a tented wedding on Martha’s Vineyard years ago, the power went out in the middle of the reception.
Instead of panicking, our sax player and drummer jumped into the crowd and started playing completely unplugged, hyping everyone up until the electricity came back.
When the lights finally returned, we went crazy with a high energy dance set.
On the flip side, I once performed at a wedding where the bride was extremely overwhelmed and arguing with her new husband and several guests throughout the evening.
There was even a real-life wedding crasher!
It was chaotic from start to finish, and the tension in the room was impossible to ignore.
Your mindset as a couple truly sets the tone for the entire event.
I had my own lesson in flexibility when planning our wedding.
Originally I envisioned a full 90s–2000s themed DJ dance party after our jam session. Even after adding an extra hour to our timeline, there simply wasn’t enough time.
So I had to let that idea go.
And honestly, everything still turned out exactly as it should, and that jam session was properly "jammin"!
Prioritizing What Truly Matters
After witnessing more than a thousand weddings, I can tell you that guests barely notice things like:
Napkin colors
Fonts on invitations
Stationary details
Flowers (sorry!) - unless they're REALLY spectacular
What guests actually remember are three things:
The music
The food
How the experience made them feel
For our wedding, our priorities were simple:
Great music
Connection with family & friends
A relaxed timeline
Not feeling like we were at "work"
Donut Wall!
I was almost “allergic” to the idea of creating a wedding that felt like the thousand others I had worked.
I wanted it to feel like ours.
That said, I still had my moments.
At one point I became oddly obsessed with the courtesy baskets in the bathrooms.
I always notice them at weddings - whether they’re stocked with great items or totally empty.
Because we had a jam session reception, we actually put guitar picks in the courtesy baskets!
The Role of Music and Atmosphere
As someone who has spent two decades performing at weddings, I can confidently say that music shapes the entire energy of the night.
The difference between a great dance floor and a dead one usually comes down to two things:
A band or DJ who knows how to read the room
The bar being close to the dance floor
If the bar is in a separate space, people naturally drift away and the energy splits.
Energy also stays high when the couple is fully present on the dance floor.
Guests take their cues from the newlyweds.
If the couple is having fun, guests feel permission to party.
We get it - classic songs like Dancing Queen, I Wanna Dance with Somebody, and Shout will almost always fill a dance floor.
But for our wedding, we wanted it to feel very different.
Our jam session featured songs by Erykah Badu, Smashing Pumpkins, Huey Lewis, Warren G, Tom Petty, Beastie Boys, The Who, The Police and many more.
During breaks, we played old-school hip hop.
My advice to couples?
Decide early whether the dance floor is primarily for you or for the entire guest list.
Trying to satisfy 150 different musical tastes is not for the faint of heart.
Give some love to your open-format DJ or live wedding band - the struggle is real.
Building the Right Support Team
Behind every smooth wedding is a team of vendors who communicate and collaborate well.
The best vendor teams don’t just focus on their own role - they’re invested in the success of the entire event.
One small tip I’ve learned over the years: pay attention to how organized vendors are from the beginning.
Are their proposals detailed?
Are their planning forms clear?
Do they communicate well?
Interestingly, vendors who require very small deposits are sometimes the ones most likely to substitute another performer or vendor if something “better” comes along.
Quality professionals tend to be transparent, organized, and invested in your event.
For our wedding, many of our vendors were friends or colleagues in the industry - what we affectionately call “friendors.”
That trust made everything much easier.
Self-Care During Wedding Planning
Wedding planning is joyful - but it can also be exhausting.
At first, I tried to plan everything myself.
But because weddings are literally my profession, the process started to feel like I was working another job - in the middle of my busiest season of the year no less!
Then we had to make a last-minute venue change, and the tasks piled up quickly.
That’s when I hired a planner I had worked with before as an entertainment vendor.
She was a lifesaver.
My husband and I also made a point to unplug from wedding planning whenever we could.
The week before our wedding, we took a spontaneous trip to the U.S. Open in New York because we both love tennis.
Sometimes you just need to step away from seating charts and timelines.
Wedding planning fatigue is very real.
Final Thoughts
If I could give one piece of advice to every bride, it would be this:
Do it your way.
They’re not exaggerating when they say the day goes by in the blink of an eye.
The details matter far less than how you want to feel on your wedding day.
Focus on creating meaningful moments, honoring traditions that matter to you, and surrounding yourself with people who genuinely support you.
And if your nephew accidentally steps on your cathedral veil during the recessional?
Rip that thing off and keep dancing down the aisle!
Vendor Team
We were incredibly lucky to have so many talented friends and friendors help bring our wedding day to life!
Venue: Stevens Estate - North Andover, MA
Partial Planning / Coordination: Slope to Coast - Elisabeth Accardi
Photography: Black Mill Photo - Manchester, NH - April Piotrowski
Videography: Neil Letendre Productions - Neil Letendre
Live Irish Music: Sean Clohessy
Ceremony Sound: Joseph & Erika
Band: Friends & Family!
Sound & Lighting: Boston Common Band
Digital Selfie Station: Pyra Agency
Audio Guest Book: After The Tone
Mobile Irish Pub: The Wandering Druid
Catering: Fireside Catering - Burlington, MA
Bar Service: Fireside Catering - Burlington, MA
Florals: DIY
Hair: Bailey Halloran
Makeup: Coley Jane
Donut Wall: DIY
Donuts: NH Doughnut Co. - Bedford, NH
Officiant: Ananda Nakira - Friend of the couple
Boston, New England and Nashville Wedding Entertainment
Planning a wedding in Boston, New England or Nashville and looking for live music, a DJ or a combination of both?
Our team at Joseph & Erika provides ceremony musicians, cocktail hour music, live wedding bands, DJs and hybrids who specialize in keeping dance floors packed all night.
👉 View our wedding music and DJ packages here: Joseph & Erika
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