Katie and Jonathan met on Coffee Meets Bagel and, from the very beginning, their relationship was full of personality and shared enthusiasm. That energy carried straight into their wedding planning, where Katie—an incredibly creative high school choral director —arrived at our first meeting brimming with ideas for how to make the day uniquely theirs.
One of the most standout elements? The florals.
Katie was passionate about designing much of the floral herself. While this is something we typically approach cautiously, her excitement was undeniable—so we worked together to create a plan that allowed her to be hands-on without adding stress to the wedding day. She designed a stunning faux floral ceremony arch in advance, and with the help of her friends, assembled fresh floral centerpieces the day before the wedding. To ensure everything came together seamlessly, we partnered with a setup team to transport, install, and later strike all floral elements. And for the most important piece, her bouquet, we brought in Steve’s Flower Market to create something truly special. The result was the best of both worlds: a deeply personal floral story, executed with professional support.
The wedding weekend began with floral prep at their apartment before transitioning into a rehearsal dinner at Longman & Eagle, setting the tone for a relaxed and joyful celebration.
On wedding day morning, the energy was light and happy as Katie and her bridesmaids gathered at the Kimpton Gray Hotel. Hair by Krista Hertzel and makeup by Austin Mark created polished, elevated looks while the group enjoyed breakfast and those quiet, anticipatory moments before the day officially began.
Katie’s bridal look was classic with a modern twist, while Jonathan complemented her perfectly in a navy tux with sleek black lapels. The bridesmaids brought Katie’s vision to life beautifully, each selecting gowns within her sophisticated color palette—deep emerald, blush pink, rich merlot, and slate blue—creating a look that felt cohesive yet individual.
Before heading to the ceremony, the couple shared a first look at Three Dots and a Dash, one of the most unique settings you could imagine. After that emotional moment, they toasted with daiquiris alongside their wedding party—a playful, celebratory pause that perfectly captured their personality. From there, they headed out for portraits around the city, including stops along LaSalle Street and the river, before making their way to The Wellsley.
Back at the venue, the Five Grain team oversaw the arrival and installation of Katie’s floral vision, ensuring every piece—from the arch to the centerpieces—was executed exactly as planned. Guests began to arrive as music from Toast & Jam set the tone for the ceremony.
The ceremony itself was heartfelt and intimate, officiated by a close family member, adding an extra layer of meaning to the moment. Following the ceremony, guests moved into cocktail hour while the room was transformed for dinner.
One of the most special touches of the evening was the couple’s decision to assign specific seats for each guest. With exactly 100 attendees, this level of detail was not only manageable, but incredibly impactful—encouraging new connections and showing just how thoughtfully Katie and Jonathan considered every person in the room.
Before joining cocktail hour, the couple snuck away for a few quiet moments together in the upstairs lounge—complete with hors d’oeuvres and their now-signature daiquiris—giving them time to take it all in before the celebration continued.
Dinner flowed seamlessly, with catering by BOKA Catering and heartfelt toasts from family and friends that highlighted the couple’s story and the deep connections surrounding them. As the evening transitioned into dancing, Toast & Jam kept the energy high and the dance floor full.
Behind the scenes, this wedding was a true example of thoughtful collaboration. Katie brought incredible creativity and vision, and our role was to help shape that into a plan that felt both meaningful and manageable. By balancing hands-on personalization with strategic support—whether coordinating floral logistics, managing transportation, or guiding the overall timeline—we ensured that Katie and Jonathan could be fully present throughout the day.
Katie and Jonathan, it was such a joy to be part of your celebration. Your wedding was vibrant, thoughtful, and filled with so much love—we were honored to help bring it all together.
