Andrew and Jessica met in 2012 when she went to Richmond, Virginia to celebrate her 21st birthday. A mutual friend that was attending the festivities brought Andrew along in hopes that they would hit it off. After the birthday weekend Andrew asked Jessica on a date. Jessica had a trip planned to Guatemala already scheduled so they were unable to make it work. When she returned stateside he quickly messaged her about meeting up.

While Jessica was away Andrew had time to plan out the perfect date starting off with seafood dinner near Downtown Fredericksburg. They hit it off and decided to extend the date by going to get dessert at Carl's Ice Cream which is a local favorite. To top off the date Andrew drove them across the river to Chatham Manor. Jessica was happily surprised with his final stop. The old manor and grounds were beautiful with gardens in full bloom. While she had never been there Andrew had and he was full of knowledge regarding the history of Chatham. They walked, talked and they enjoyed the rest of their ice cream against a gorgeous sunset that overlooked the Rappahannock River and Downtown Fredericksburg.

Jessica had been waiting for what felt like forever for Andrew to finally pop the question. They had been together for 8 years after all. Andrew had always said he would never propose in December as the month is always busy with birthdays and holiday festivities. Knowing that Jessica was not expecting anything out of the ordinary to happen. After a long and tiring semester of hybrid teaching Jessica went to happy hour with coworkers to celebrate surviving school and finally having a much needed break. After a few drinks Jessica decided it was time to go home and take a power nap. Little did she know that Andrew had a special weekend planned for them. The original plan was to have whisked Jessica away to Virginia Beach for the proposal. However, Andrew was nervous and is not good with keeping secrets so he had to adjust his plan a little. While she was watching a Christmas movie Andrew came out to the living room with both fur babies in hand and got down on one knee. In their first home with their first fur babies Andrew asked Jessica to spend forever with him and she said "Yes!". He further surprised her with the news that they would be leaving first thing in the morning for Virginia Beach to celebrate their engagement with friends.