One Sunday in August, following the Falmouth Road Race in Cape Cod, Kevin and Elizabeth met at a backyard cookout at Elizabeth's grandmother's summer home. A month later, they saw each other at a birthday party where their brief reintroduction turned into making plans to see each other again.

After dating for close to two years, Kevin and Elizabeth had plans to meet Kevin's brother, Joe, for dinner on Friday night. Before meeting Joe at Kevin and Elizabeth's first date spot, Kevin asked Elizabeth to walk Castle Island, a peninsula in South Boston. Since Elizabeth was late (two hours!) due to a work matter, Kevin squeezed in the big question at dusk with a few of Kevin's siblings close by.