How She Asked: A Family-Centered Surprise Marriage Proposal

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How we met: You know how all the greatest love stories start with “One day, long, long ago”…? Well, that’s exactly how ours began- with every moment of our past leading up to the chance that would finally bring us to THE ONE. We had both known love, good love, in fact. But a truth occupied the life within those past relationships, an unsettling, nagging sense… an absolute certainty that there had to be something more. So perhaps unknowingly we had been sending this powerful wish out into the universe, never knowing what the answer would be but always having faith. Then, serendipitously we stepped into each other’s lives; Ilene called in to work a shift she wasn’t supposed to and I, pulled out from sleep and forced out for the evening.

We had no clue how much that one night would turn our worlds around! We struggled not to fall in love, but what we felt continued to grow deeper and stronger, becoming everything we had ever wished for. So many people, even to this day, will say how the energy between us could be felt even if we were across the room from each other. As you know, love refuses to be ignored. So unquestionable and intense, we could no longer deny it and we were not willing to risk losing this gift the universe had presented to us.

We made a commitment then to be true to ourselves, our love, and our families. The early years of our relationship were deeply emotional; we endured rejection and cold shoulders to find the warm embrace of devotion and support, we filtered through intolerance to find acceptance, we sifted through pain and hostility to find magnificent truth in love. We’ve come a long way from the day Ilene first told her two daughters about our relationship and we’ve worked very hard to become a family over the years. One of the most important roles we have is raising two teenage girls, and consideration of their overall well-being was also the reason this proposal was eight years in the making. I had known instantly I wanted to spend the rest of my life with Ilene, but I also knew becoming a family would take time, effort, and patience- a whole lot of patience. But it has definitely paid off!!

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How They Asked: About a year ago I worked up the courage and asked for the girls’ blessing to marry Ilene. Since then we’d been planning every element that would go into the perfect proposal for their mom. The girls were in on all the details, even helping me design the engagement ring! It was getting close to the planned proposal date and all the final matters were being put into place – but then everything changed. We learned that Ilene’s youngest sister, Michelle, had landed a job in California and would be moving 2100 miles away… in less than a month.

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It’s important to understand here – we could never begin to describe how deeply we cherish those who have given us their unconditional love and support – Michelle and her husband Will have stood up to defend our relationship and play an integral part of our support system. They had to be there for our engagement. I realized I had to change all my original plans, and it all had to be done quickly. Suddenly the proposal date was moved up almost 2 months earlier than planned. I worked fast, first notifying the jeweler I needed the ring ready in half the time it was scheduled to take.

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Using a family photo session as a cover was the perfect way to deflect any of Ilene’s suspicion and still include the people we love to be part of that special moment. Ilene’s sister Jacqueline helped make arrangements with the photographer, who also happened to be an old high school classmate. I asked close friends and family to make short videos sharing their thoughts on our relationship. The girls spent endless hours with me putting together videos, photos, and a ridiculous amount of trips to more stores than I can remember. Close friends helped me figure and test out various aspects of the video equipment to ensure there would be no technical difficulties. Since Ilene had classes four nights out of the week, this all remained easily hidden from her – we were scheming ninjas, able to accomplish all our covert operations right under her nose!

I had everything set in place… well, almost everything. Did I mention her custom engagement ring hadn’t even been completed by the jeweler yet? It wasn’t until 8pm the night before the proposal was all set to happen that I received confirmation her ring was finished and on its way from Seattle, WA. With less than 18 hours to be shipped and arrive to it’s destination outside of Chicago, IL… can you say ‘major stress factor’?!!? I swear, I almost forget to breath a few times within those hours. Yet just as fate would play it out, her ring arrived on the doorstep that morning. Literally.

We had Ilene believing the equipment was for a farewell video for her sister and brother-in-law. During the car ride into the city she continually argued against the need to lug around all the gear, asking if we could just view the video with them later or insisting she help me carry the equipment from the parking spot (she happens to work with attorneys, maybe that’s why she loves arguing so much). However, I had also arranged for a different group of family and close friends to rendezvous at the parking garage, so I couldn’t allow her to help me. I managed to politely ignore her reasoning and dropped off a frustrated and clueless girlfriend at the entrance of Chicago’s Lincoln Park, where her family and the photographer were already waiting. Starting the family photo session, I had hoped my nerves would settle with all the distractions. On the contrary, as we got closer and closer to the predetermined proposal site, my heart raced faster anticipating the signal I had worked out with the photographer. Suddenly there it was-the signal! Rushing to set up the equipment with shaking hands, her daughters and I managed to get the video started.

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Just as planned, Ilene stood in front of the monitors watching the first few pictures of her sister and brother-in-law come across the screen.

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I looked on as the pictures switched to show scenes of her and I and confusion played across her face.

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I watched as the other group of family and friends raced wildly across the park, eager to witness this moment. The whole time, I stood in awe, realizing what was truly happening.

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I still couldn’t believe this moment was finally here – through countless tears and trials and years spent hoping…here we were, listening to our family and friends share how much they loved us, how inspiring and beautiful our love is.

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This was the moment we had both been dreaming of. This was the moment I held her hand in mine and the time stopped just for us. My voice spoke for my heart, declaring how my world had been completed the day we’d met, asking her to share a future with me.

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This was the moment she said, “Yes!” Our love grows, continuous as true love does, honestly, completely, and all encompassing. The kind of love that can make the whole world go silent just looking at her. Our love story started long before fate caused our paths to cross – and we continue to create a path for it, always working to keep it the greatest love story of all time.

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Photos by Cassandra Photo