After a day filled with bourbon, horses, and sunshine at the racetrack, Patrick and his friends, visiting Lexington from Cincinnati, refueled for the evening at a local wing joint. Shannon received a text from her friend Kelsey who invited her to join the group and finally meet the guy Kelsey had been telling her about. As Shannon walked into the restaurant in her scrubs, straight from work, the group shuffled seats purposefully, leaving the only open seat next to Patrick. The night progressed from dinner to dancing, and sparks flew as Shannon and Patrick individually realized how compatible they were. Before the visit ended, Patrick confidently disclosed to Shannon that he would like to take her on a date. Impressed by his forwardness, Shannon agreed to the invitation and drove up to Cincinnati the next week for an evening that, unbeknownst to her, would be the first date with her future husband.

Patrick arrived on Anna Maria Island, ring box in hand, with a plan that he, his family, and Shannon's family had been devising over zoom calls and group messages for several weeks. A few days prior, Shannon had arrived on the island, excited for a low-key weekend with her parents and sister, Samantha. Shannon was under the impression that Patrick was unable to join her on the weekend getaway due to work responsibilities, so she was blissfully unaware of the events that were about to take place. The next afternoon, Shannon was encouraged by her family to find the perfect spot on the beach to take a family photo and have a glass (or two) of wine. As Shannon ran toward an area of untouched, sandy beach, she saw a handsome guy in a suit emerge out of the corner of her eye. Shannon was so genuinely surprised she stopped dead in her tracks and yelled, "Patrick!? What are you doing here?!" After a short walk on the beach, hand in hand, he got down on one knee and asked Shannon the easiest question she had ever answered. Remembering that they were not the only two people on the beach, Shannon looked around and saw Patrick's parents, Janet and Greg. They had flown in from Houston and were walking toward the couple with Champagne. Shannon's parents, Paul and Deb, embraced the newly engaged couple and expressed gratitude that they no longer had to keep such a huge secret from Shannon. Pam O'Connor, a close family friend and talented photographer was kind enough to join in on the surprise and capture the priceless moments. The celebration continued all weekend, and it was undeniable that the Dwyer and Winebar families were almost as compatible as Shannon and Patrick.