Delightful Chicago Engagement | Catie + Jack


Once upon a serendipitous swipe on Bumble over the Thanksgiving holiday in November 2019, Jack and Catie found themselves entwined in a delightful digital dance that would lead them to a lifetime of shared laughter, quirky surprises, and a love as genuine as the most heartfelt Broadway ballad.

Catie, with a discerning eye, was drawn to Jack’s online persona—a canvas painted with love for friends, family, and the fervor of Chicago sports. However, it wasn’t merely the familiar passions that ignited Catie’s interest but a particular quirk that set Jack apart—a penchant for the Irish exit. There was something intriguingly charming about a man who knew when to gracefully bow out of a social gathering.

That nuance sealed the deal for Catie, prompting her to make the first move. Little did she know, this digital connection would evolve into a love story filled with surprises and shared joy.

Jack, equally captivated by Catie’s infectious laughter evident in every picture and her unique passion for the perfect amount of golf—12 holes, to be precise—found himself entangled in a delightful mystery. The intrigue deepened as they got to know each other, discovering the magic that happens when two individuals authentically embrace their quirks.

The turning point in their journey, the moment they both knew they were destined for each other, unfolded in a blend of Christmas magic and classic cinema. Jack, the orchestrator of a memorable proposal, took advantage of Catie’s involvement in planning the holiday party for Shedd Aquarium’s Auxiliary Board in December 2022.

Amidst the modest budget discussions and Catie’s stress as a perfectionist event planner, Jack discreetly plotted the perfect proposal. After a brief appearance at the party, he disappeared only to reappear by the belugas, bathed in spotlight, ready to profess his love and commitment on one knee. It was a moment that encapsulated the essence of their relationship—surprises, shared passions, and the promise of a lifetime together.

Jack reminisced about the pivotal moment that solidified their connection, “It was right before Christmas, and I went all out and planned a nice dinner before a showing of ‘It’s a Wonderful Life’ at the Music Box Theater, an old-school cinema in Chicago. There was a sing-a-long, the Christmas spirit was high, and I could tell we had something special.” The magic extended beyond the silver screen as Jack discovered Catie’s love for popcorn, a discovery made memorable as she insisted on taking a giant tub with her on the cab ride home—a testament to the goofy and endearing qualities that brought them closer.

Catie, reflecting on her realization that Jack was the one, painted a vivid picture of a summer Friday night in July 2020. A shared love for Broadway brought them together to watch “Hamilton,” a production she held dear having seen it four times. However, it wasn’t the Broadway magic alone that sealed the deal but the way Jack embraced her quirky surprise. “When I opened the door wearing a white colonial wig, a patriotic scarf, blasting the show’s soundtrack, and equipped with themed cocktails to set the mood, Jack got such a kick out of the surprise.”

It was in that moment, amidst laughter, shared enjoyment, and mutual acceptance of each other’s quirks, that Catie knew they were meant for each other.

Their engagement, a culmination of shared experiences and authentic connections, sets the stage for a lifetime of love and laughter. As they embark on the journey toward marriage, friends and family eagerly await the day when Catie and Jack say their vows, ready to witness the continuation of a love story filled with surprises, joy, and the beautiful authenticity that defines their relationship. May their wedding be a celebration of the unique bond they share, and may their lives together be a testament to the enduring power of true love.