Most Common Wedding Planning Mistakes (And How to Avoid Them)

We’re not here to scare you — promise.
But after planning countless luxury weddings in Chicago (and beyond), we’ve seen firsthand how even the most well-intentioned plans can go off-script. The good news? A great planning team can handle almost anything — and sometimes, a little flexibility, preparation, or just plain common sense can make all the difference.

We’re sharing a few real-life planning hiccups we’ve witnessed over the years — and the simple takeaways that could save your day.

1. When the Bride Was 30 Minutes Away… and So Was the Ceremony

One sweet couple insisted on staying off-site until the very last minute — and unfortunately, their limo driver (not one of our recommended vendors!) took a very wrong turn. The bride and her entire party ended up at the wrong location, over 30 minutes from the actual venue.

Because we had built a 45-minute cushion into the timeline, we were able to recover: we shortened cocktail hour, had the officiants gently tighten up the ceremony, and kept guests informed along the way. The bride stayed calm, the vendors adapted, and the couple still had a joyful, smooth evening.

Lesson learned: A thoughtful timeline isn’t about being rigid — it’s about leaving room for the unexpected. That buffer? It’s your best friend.

2. The Cake Was Cracked... So We Turned It Around

On the way to a wedding, we got a call from the venue — the cake had a massive crack in it, and the bakery had already left. When we arrived, it was clear there was no salvaging it fully.

So what did we do? We pivoted (literally). We rotated the cake so the damaged side faced the wall, adjusted the floral placement and lighting, and had the couple do photos and the cutting on the “good” side. Guests never even noticed. No need to panic or upset anyone!

Lesson learned: Not everything can be fixed, but a creative solution can still save the moment. That’s what good planning (and a calm planner) is for.

3. Two Coolers, One Church Bus, and a Lot of Rolling Cans

We had a group of groomsmen who were very ready to celebrate — so much so that they brought two full coolers of drinks onto the shuttle. As they climbed aboard, one cooler burst open, spilling ice and cans everywhere — just barely missing the photographer’s gear bag.

Cue the planner scramble: we mopped up the ice, retrieved runaway drinks from under seats, and made it to the church on time. But the fun didn’t end there — the second cooler exploded again at the reception venue, and at that point, we handed the guys a trash bag and told them to get to work.

Oh, and none of them used the bathroom before the ceremony, so we watched them file out one by one during communion to wait in line for the single-stall church restroom.

Lesson learned: Pre-ceremony drinking (and hydration) needs a little forethought — and drinking on party buses in Chicago can actually lead to city citations. Best to keep it simple (and spill-proof).

(photo has been filtered to protect privacy)

4. That One Time a Wedding Dress Had to Be Washed in a Sink

New Year’s Eve in downtown Chicago sounds like a dream for wedding portraits — until slush gets involved. One of our brides was taking photos before her ceremony and ended up with the entire train of her gown coated in Chicago street grime. By the time she reached the venue, the dress needed some serious attention.

With quick thinking (and cold water only — no soap or stain remover!), we were able to scrub out the dirt in the venue sink while she wore it. Her bridesmaids sent the groomsmen racing back to the hotel for hair dryers, and miraculously, we dried the train before her walk down the aisle.

Lesson learned: Think carefully about how your portrait locations might affect your attire. Work with your planner to build in extra buffer time — so if something goes awry, there’s room to fix it without panic.

Final Thoughts: It’s Not About Perfection — It’s About Preparation

Your wedding won’t be perfect. No one’s is. But when you have a trusted team, a realistic timeline, and the flexibility to roll with the unexpected, it can still be everything you dreamed.

At Sholeh Events, we’re big believers in planning for joy and in planning for the curveballs. We hope these stories help you feel empowered to approach your day with clarity, confidence, and a sense of humor — because if nothing else, you’ll walk away with some great stories of your own.

Want more tips on how to avoid the overwhelm?
👉 Check out Our Wedding Coordination Services
👉 Or read: Escort Cards? Place Cards? Seating Cards? What is right for my Wedding?

Contact us for a custom proposal

If you’re looking for a calm, capable team to help guide you through the highs, hiccups, and hilarity of wedding planning — we’d love to meet you. Reach out here, and let’s start planning your day, your way.

(Note, photos included to illustrate the post - no guilty parties here!)

Real Stories, Real Lessons — From the Sholeh Events Team
By Sholeh Events