Love at first sight couple gets engaged on the Navy Pier in Chicago, Illinois during the frosty wintertime

Real Engagements: Shelby & Winston

By Mae Wagner

bride to be Shelby engagement engaged fiance fiancee Winston proposal proposed Chicago Illinois Navy Pier winter love and first sight

Shelby wasn’t sure if she believed in love at first sight until she spotted Winston on Christmas Day in 2015 at a mutual friend’s house. She had been invited over to celebrate and meet members of the football teams who played for the University of Minnesota, in the Quick Lane Bowl. Winston was there that day with his teammates. As he sat back casually watching television, Shelby caught a glimpse and was blown away by his swagger, which stood out to her in the room full of other men. At that moment she felt in her heart that she may have just found the one, strangely enough. Once the two were introduced, there was an instant chemistry. It didn’t take long for Winston, who was nicknamed “Geech” by his teammates, to make her laugh non-stop, and Shelby knew that the connection she had originally felt was real. Initially, Shelby believed that this situation was too good to be true; she was only 17 and worried that Winston was older, but when she found out that they were actually the same age, she was overjoyed. After the festivities ended, Shelby drove several of the football players back to their hotel, Winston included. During the group discussion, one of Winston’s teammates said to him, “wow Geech, this might be your wife,” seemingly sealing the duo’s fate. After exchanging numbers, Winston promised Shelby that he would see her again. However, there was still the issue of them living in different states. Shelby was from Detroit, MI, and was attending Western Michigan University, while Winston went to the University of Minnesota but was raised in Baltimore, MD. Thankfully, their love knew no bounds and they stayed committed in their relationship.

Seven years later, Shelby, a social media coordinator, and Winston, a college football coach, had just moved into their apartment in Akron, OH. It was winter and nearing their three year dating anniversary. Winston devised a plan that would include a proposal and scheduled a trip to take Shelby to Chicago, IL under the guise of seeing his best friend and former teammate receive an award there. When they arrived in the city, Winston told Shelby to look her best because they would be taking pictures before the event. When they arrived at the chilly Navy Pier, they met a photographer who instructed Shelby and Winston to walk to the edge of the water in order to get better natural sunlight. When the photographer told Shelby to turn around, she was shocked and delighted to see all of her friends and family surrounding them gleefully taking pictures with their phones. She turned to see Winston pulling a ring box out of his pocket. As she began to cry, Winston said, “didn’t I promise you that I would see you again?” He went on, “I’ve always kept my promises and now I’m going to make you this promise,” as he got down on one knee and asked her to be his wife.

Shelby and Winston plan to wed in March of 2024 at a destination wedding in Jamaica.