Matt was unsure if he wanted to attend a dinner party that his friend Luis invited him to for the birthday of a friend of Luis's. Matt decided he needed to get out more and told Luis he was in. Matt and Luis were the first ones to arrive at Graziano's in Coral Gables and took their seats at the large table awaiting the other guests. Not long after an elegant, tall, red-haired woman sat down across from the two guys and introduced herself as Kelly. The group spoke at length as they waited for the birthday girl to arrive. When the food came, Matt even offered to share some with Kelly. (This would be the first of many meals they would share.) After dinner, the group went dancing at the famed Ball & Chain on Calle Ocho. Matt began the festivities with a round of drinks. The night went on as Matt attempted to teach Kelly a few salsa steps he knew, but before the night was over Kelly remembered she owed Matt a drink. She bought two Moscow Mules, one for him and her. Matt had bought drinks for girls many times in the past, but this was the first time a girl had ever bought one for him in return.
Kelly has always known the ways she did not want to be proposed to: at a sporting event, putting the ring in food, or even at Disney World. All those options were off the table. This left Matt to get creative. So as he often does, he found creativity in the creativity of others. Kelly's friend Corinne had masterfully planned a trip to St. Lucia for her own 30th birthday. Matt knew this would be the perfect place to pop the question. He set it up with the resort they were staying at, arranged for a photographer to memorialize the event, and, of course, made sure it was ok with Corinne to do all this during her birthday trip. Kelly was dressed beautifully as the trip group had planned to do a wine tasting and dinner that night. Then, in the middle of the longest wine tasting anyone had ever been to, Matt asked Kelly to step outside. He led her to the resort's veranda overlooking the ocean, and it was there that he got down on one knee and asked her to spend the rest of their lives together. Tearfully she said yes, and the two of them and the rest of their friends on the trip celebrated into the night.