Love in Bloom

By Lisa Arnett
May 2025 View more Better Together

From first date to wedding day, this couple kept Naperville close to their hearts

Maddy Gerald and Sean Ashley’s first date in December 2019 packed in a lot of activities: dinner at Lou Malnati’s, strolling around downtown Naperville, drinks at Solemn Oath Brewery, then a leisurely drive looking at holiday lights. When they still weren’t ready for the night to end, “We decided to watch movies, and he let himself out after I fell asleep,” Gerald says.

After that first date, Ashley couldn’t help but see Gerald’s name everywhere—literally. Her family operates 14 car dealerships in the Chicago area (including Kia, Subaru, and Nissan locations in Naperville) and the Gerald name is easily spotted on license plate frames around town.

In addition to teaching special education at her alma mater, Neuqua Valley High School, Gerald also coaches for Special Olympics. Ashley, a Naperville Central and Northern Illinois University grad, works in the insurance industry.

As a callback to their first date, Ashley proposed to Gerald four years later, after a pizza dinner at Lou’s. “It was pouring rain, but I somehow convinced Maddy to walk with our umbrellas to the Riverwalk,” he says. After he popped the question at the covered bridge, they toasted their engagement at Solemn Oath, where friends were waiting to surprise them.

They kicked off their Naperville wedding weekend in November 2024 with a welcome party at Hugo’s Frog Bar, and the next day married at The Crawford in the company of 195 of their loved ones. Gerald had envisioned being married under a display of blooms suspended from the ceiling, so wedding planner Amy Reifenstuhl of Rustique Swan Event Design & Curated Decor collaborated with Aysel Cristian Floral Atelier to bring Gerald’s plan to life.

The couple’s first dance to “Simply the Best” by Billianne was a complete surprise to their guests and the culmination of many hours of rehearsal. “We took 10 weeks of classes at Dance Fun USA [in Naperville] and had a fully choreographed dance that we practiced in our garage,” Gerald says. “It was very much out of our comfort zone, and we had never done anything like that before.”

To commemorate the night, guests left audio guestbook messages on a vintage rotary payphone from FêteFone and took photo booth snapshots with Alfresco Photo, all fueled by late-night slices from Lou’s.

Wedding Details

Bride’s attire
Essense of Australia gown from The Crystal Bride, Geneva

Bridesmaids’ attire
Dessy dresses from Bella Bridesmaids, Oakbrook Terrace

Hair and makeup
Brittany Grist of Patty McGuire Hair & Makeup Artists; Kelly Grist of Manic Beauty

Groom/Groomsmen’s attire
Tuxedos by Generation Tux, Chicago

Rings
Hers by Rendrag Jewelry, Philadelphia; his by Manly Bands

Menus and programs
Greenstar Paperie, Downers Grove

Catering
Chef By Request, Lisle

Cake
GeGe Bean Sweets & Treats, Montgomery

Entertainment
The Upbeat Band, Chicago

Photographer
Jason Verdin Photography, Chicago

Photos: Jason Verdin Photography