On February 13th, Kevin had set-up a surprise date for Eliza under the guise of Valentine's Day plans. To start the day, they went to the Isabella Stewart Gardner Museum. Little did Eliza know, while they were at the museum, both of the families came to their Allston apartment to decorate and get ready for a dinner to celebrate after Kevin popped the question. Eliza and Kevin left the museum, and Kevin told Eliza he had a small pit stop planned before dinner. Eliza was hoping it would be a hot chocolate since it was a very chilly day. Instead, Kevin brought her to a special spot from their first date, Castle Island in South Boston. The couple traversed through the snow to sit on the bench they'd sat on together during their first date, watching planes take off from Logan and getting to know one another. Kevin finally got the nerve to ask the question, with the families sitting in their cars at the other end of the beach. Eliza was surprised to say the least, and so excited to share the special moment with the families. They all headed back to the Allston apartment where Eliza was surprised again to see the decorations and dinner plans. The night was filled with smiles, Italian food, and best of all, Eliza's mom's beautiful homemade cake.