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Tyler Loeb

and

Taylor Hickman

March 13, 2026

New Orleans, LA

Our Engagement Story

Written by Tyler Loeb

I knew I wanted to marry Taylor early in our relationship. When I was with her, I felt more like myself than when I was alone—it was freeing in a way I’d never felt before. I thought this might be heightened by the work I was doing on myself post-pandemic, but the feeling never went away. In fact, it grew stronger as we deepened our relationship. As time passed, we moved beyond the initial excitement and into more honest, challenging conversations. I found myself reflecting on past experiences with a deeper understanding, something Taylor helped me unlock. This emotional growth strengthened our bond and continues to make it unbreakable. Three years into our relationship, I was ready to propose. Luckily, our friend's dad, Alan Cobb, is a talented jeweler. Taylor and I visited a few stores to get a sense of what she liked, and Alan crafted the perfect ring for me. The ring was created, but the proposal was still six months away. I planned to propose on the beach in St. Augustine, a place that held sentimental value for me because my family vacations throughout the years have always been there, but also my parents were engaged on the beach. But then, I thought San Francisco could be an even better opportunity. It reflected our love for spontaneous travel. I planned a perfect trip: a hotel with a rooftop sunset view, a convertible, wine country drives, and hikes to see the Golden Gate Bridge. The trip ended up stressing me out. I carried the ring around, trying to find the perfect moment, but it was either foggy or crowded. Our most romantic moments were at vineyards, while the ring stayed in the car. I even booked a rooftop reservation for sunset, but we were seated inside. After begging the maître d’, we were moved outside, but it was crowded with people taking photos. The atmosphere wasn’t right. Taylor asked me several times if something was wrong because I seemed distracted. I realized I had been so focused on crafting the perfect proposal that I’d lost sight of enjoying the trip. I knew I needed to simplify things and do something I had more control over. After returning from San Francisco, I realized a birthday party for Taylor at our friend Bridget’s house would be the perfect opportunity. Taylor would be dressed up, her friends would be there, and Bridget’s house was near City Park, a special place to me. I chose Langles Bridge in the park and enlisted Taylor’s best friend, Andrea, to be our secret photographer. I had one last challenge: getting the ring out of the large box. After several failed attempts to buy a smaller box, I lucked out when a store gave me one for free. On the day of the party, I convinced Taylor to spend some quiet time with me in the park before we went. We sat in the heat on a blanket, enjoying wine, while I texted Andrea to make sure she was in position. I suggested we take a walk toward the bridge. As we approached, I saw Andrea, disguised as a spy, sneaking into place. I distracted Taylor by pointing out turtles in the pond. I led Taylor to the top of the bridge, and as we waited for Andrea to get into position, I realized I hadn’t said anything for a while. Taylor asked if we could head to the party. I turned her around, began fumbling for the ring, and started my speech. When she saw what was happening, her jaw dropped, and tears filled her eyes. I got down on one knee, asked her to spend forever with me, and she said YES! The park cheered, and we shared a sweaty kiss before laughing about Andrea secretly taking our photos. It was a dream come true. City Park had so many memories for me, and I was thrilled to add this moment. We went to Bridget’s house to surprise our friends with the news. Every time someone entered, we’d shout, “We’re engaged!” My parents gave me family rings from my grandparents, even my great-grandma, Heddy. Alan will melt down the gold from these heirlooms to create our wedding bands, which makes the moment even more special.

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