How Did One of Milwaukee’s Best-Known Party Planners Approach His Big Day?

With gusto!

The only must-have for a memorable wedding is love – unless you happen to be a prominent wedding planner with a stellar reputation to uphold. Dynamic Events founder David Caruso took everything he learned in his 17 years in the business, then kicked it up several notches when it came time to stage the most personal wedding of a triumphant career: his own.

On a Friday in September, 200 guests arrived at the Hilton Milwaukee City Center hotel to greet one another over celebratory drinks. Then they were whisked onto a waiting bus, destination unknown to all but close family. “Have you ever been to a wedding that starts off with this kind of surprise?” Caruso teased in a prerecorded video playing on board.

Adam Steffan (left) and David Caruso strike a pose on their wedding day. Photo by Front Room Photography

Minutes later, the entourage unloaded outside the Pabst Theater and paraded down a red carpet leading through the backstage door. Inside, they took their seats on the stage, facing the cavernous red-gold auditorium. The wedding procession began minutes later, with attendants making their way down the candlelit aisle to a live rendition of “How Does a Moment Last Forever” from the stage version of Beauty and the Beast. With everyone in place, Caruso and his partner, Adam Steffan, rose to the stage via trap door, while nine chandeliers descended from the rafters. Even relatives were astonished; they weren’t told about that crucial detail at the rehearsal dinner. “On behalf of David and Adam, I welcome you to their simple, modest celebration,” deadpanned the Rev. Dr. Mark McDonough.

For Steffan, who teaches drama in Wauwatosa, getting married on a stage was fitting. And every aspect of the festivities had meaning to the couple. “We promised each other that we would be totally authentic,” Caruso says. “We are big people.”

The couple make a dramatic entrance, rising from the stage at the Pabst Theater. Photo by Front Room Photography

A wedding this orchestrated doesn’t happen overnight, even for the prince of parties. Caruso started planning the event shortly after he began dating his partner on Jan. 1, 2016. “Ever since we first met on that magical New Year’s Day, I knew that if I was given the gift to share your life that it would be the greatest honor imaginable,” Caruso said in his vows.

“On May 2, 2016, I wrote a note, really kind of a prayer, on my iPhone that says, ‘This man is meant for me. Please help us through our special journey. I know it’s meant to be.’”

Steffan was just as smitten, writing a friend after his first date with Caruso to say he found his future husband.

“As a young person, I used to wonder if anyone would ever love me,” Steffan told his spouse. “I believe you and I are meant to be.”

After the tear-filled nuptials, guests walked to the bar area for cocktails and hors d’oeuvres. In one corner, white-gloved servers dispensed glasses of bubbly from behind a gold curtain of a makeshift champagne booth at the touch of a button. Later, buses brought the party back to the Hilton, where a formal dinner was served in the Monarch Lounge. Pear salad and limoncello followed pillowy beds of lobster ravioli and goat cheese torta, all of which preceded the entrées: slabs of Wagyu beef, miso-glazed salmon and chicken braciola. A decadent pistachio budino with caramel chocolate bark finished off the meal.

A guest snaps a selfie at the Crystal Ballroom. Photo by Front Room Photography.

At 9 p.m., after six hours of merriment, a typical wedding would be winding down. But this was not your typical wedding. Instead of heading home, guests boarded the elevators to travel a few floors up. There, the doors of the Crystal Ballroom swung open to reveal a glitzy disco setting, with a live band, performers teetering on stilts and shirtless hunks writhing around in white suspenders underneath a mirror ball roughly the size of a harvest moon. Dancing and more merriment ensued.

To Caruso, who has sent so many other couples off on their happily ever after, the occasion was a long awaited and closely held dream come true.

“We’re calling this an explosion of joy,” he says. “This was the perfect way to celebrate our next chapter. We are on cloud nine.”


More Photos
Guests walk down the red carpet before the ceremony. Photo by Front Room Photography.
A glass of champagne is handed out at the press of a button. Photo by Front Room Photography.
A glass of champagne is handed out at the press of a button. Photo by Front Room Photography
A formal dinner is served at the Monarch Lounge at the Hilton Milwaukee City Center. Photo by Front Room Photography
Wagyu beef was among the entrées on the menu. Photo by Front Room Photography.
Photo by Front Room Photography.

This story is part of Milwaukee Magazine‘s Milwaukee Weddings 2020 Issue. 

Find the issue on newsstands or buy a copy at milwaukeemag.com/shop.

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