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Alyssa & Conor

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Alyssa

&

Conor

June 21, 2025

Chicago, IL

It's a love story, and baby, she said yes

It was a bright, sunny day in the middle of Co. Clare, Ireland. We were midway through an already incredible trip across the country with plans to stay at a beautiful castle-turned-hotel for one night. Driving for hours past more sheep than we could count, we arrived at Dromoland Castle where, little did Alyssa know, an incredible fairytale story was about to unfold. Shortly after arriving, Conor casually mentioned to Alyssa that his family had planned a carriage ride for that afternoon. Alyssa was surprised when Conor said she should dress for their fancy castle dinner before going on the carriage ride. She thought this was strange - naturally she was worried her hair would be ruined out in the elements - but she hurried to get ready. Upon arriving to the castle courtyard and finding a horse-drawn carriage with no other family members in sight, Alyssa realized Conor was going to propose. The carriage stopped at a gorgeous vista along the way, and Conor asked to get out and take a photo. Immediately, he reached into his pocket, got down on one knee, Alyssa instantly began crying joyful tears, and when he asked "Will you marry me?", she said "Of course I will!". A photographer, named Brian if you like the details, sprinted across the grounds to capture the magical moment. After taking pictures and finishing the carriage ride, most of which now feels like a dream, they returned to the castle to celebrate with Conor's family. Alyssa attempted to call her family, but they quickly said they weren't available to FaceTime. Alyssa was disappointed they didn't want to see her gorgeous engagement ring, but with all the excitement and celebration in store, she decided to call back later. Walking back into the hotel, Alyssa got an excited hug and congratulations from one of the hotel staff members who she quickly recognized was in on the surprise. He led them to Conor's parents' suite. Skip met the pair at the top of the stairs, with a big hug he welcomed Alyssa immediately into the family and said "Now the only thing that would make this better is if your family was here". With wide eyes, Alyssa looked further up the stairs only to be stunned into happy tears and silence as she saw her parents and sister Rebecca walking down towards her. As the shock settled, Alyssa began to learn of the elaborate plot both families had concocted to create this beautiful surprise, including multiple near-misses when the cat almost got out of the bag. Conor, along with both families, had created a true fairytale experience, right down to the castle and horse-drawn carriage. It was a proposal for the ages, and of course, she said yes.

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