Tom and Gina went with his family to Destin, Florida in February 2022. Tom and Gina are huge beach people, so Tom knew this was the perfect opportunity. Tom had told Gina a few months prior to leaving that while they were down in Destin, they were "going to surprise his mom with professional family photos on the beach" so they need to make sure they have an outfit picked out for it and to keep it a surprise. The photographer, Tom, and his family were all in on the giant surprise.

Little did Gina know, Tom had talked with her dad and asked for her hand in marriage. While there he explained to her dad and mom his proposal idea. They made plans with Gina's parents to be Facetimed by Jesap so they could be there for the proposal. Tom and Gina also go to the same hair salon. Tom talked with Elevated Hair Co and let the girls who work there in on the secret. That way Gina's hair and nails were done without her thinking too much into it.

On February 15th, 2023 the family went down to Henderson Beach State Park to have their family photos taken. Tom and Gina were getting a couple of photos done. When they were finished Gina started to walk away. Everyone was calling Gina's name to turn around and when she did Tom was down on one knee. Tom asked Gina to marry him and of course, she said yes! Jesap came up to Gina and said "Want to say hello to your parents?" Gina saw her family had seen the whole proposal. On the way to dinner, Tom and Gina Facetimed their closest friends and showed them her ring and that they were engaged. They celebrated at a restaurant called " The Back Porch". Gina will tell you "I came to the beach as girlfriend, but I left as a fiance!"

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