Jessica & Damian met in law school during their Wills, Trusts, & Estates class. Damian walked up to Jessica's desk and told her he found her attractive and wanted to take her out on a date. He wrote his number down on a piece of paper and told Jessica "text him if you would like to". Jessica text him later that day and this is where their love story began. Their first date was at the River Front in Tampa, FL and they talked for hours that night. A couple of days after that COVID-19 shutdown occurred and every establishment was closed therefore, date nights had to get creative. For example, Damian decorated Jessica's apartment with roses and transformed the patio into a romantic dinner date. As a result of their unconventional beginning, Damian knew that Jessica would be the one and shortly after he asked her to be his girlfriend.

Damian and Jessica planned a vacation to Jamaica in April of 2023. While Jessica believed it was a routine vacation, Damian had other plans. Damian planned for dinner on the beach the first night in Jamaica. After they sat down for dinner, Damian asks another guest capture their picture. Jessica stood for the picture and Damian announced that he had to tie his shoe. When Jessica looked back to see what was taking Damian so long she was shocked to see Damian on one knee. Damian asked "Will You Marry Me?" With no hesitation Jessica obviously said YES.