VIP Wedding 2022 Cassandra + Jerry


After meeting in a dive bar in Annapolis, Cassandra Maloney and Jeremiah Sullivan III dove into love, dating for just over a year before Jerry realized that it was time to dive all the way in. “He proposed on my birthday in December of 2018,” says Cassandra, who works as a commercial real estate broker, while Jerry is a security consultant. “He reserved an igloo at the Four Seasons in DC so our dog Lucy could join us. That evening, he ordered rabbit pasta for Lucy because she always likes to chase rabbits but never manages to catch them. We enjoyed a lovely, romantic dinner and after dinner, we walked along the monuments until we reached the Thomas Jefferson Memorial. He proposed in the rotunda of the memorial, which is where his father proposed to his mother. He gave me an antique ring that was around 100 years old, with sapphires, which are my favorite.”


Six months later, on June 8, 2019, Cassandra wore a lace gown with a mermaid silhouette as she walked down the aisle at St. Paul’s Episcopal to meet Jerry at the altar. Vows exchanged, they joined their guests for a buffet-style reception at Hummingbird that showcased the restaurant’s delicious food. Sweetening up the celebration, the couple opted for an assortment of ice cream cakes from Cold Stone instead of a traditional tiered wedding cake. “We love ice cream cakes, and they make an appearance in most of our special events—including birthdays,” Cassandra notes. “All of the cakes were coated in chocolate ganache and we framed our engagement photo on one cake and our first date [photo] on another cake.”

After indulging in ice cream, the newlyweds and their guests enjoyed a nighttime snack bar with French fries, mini burgers and key lime pies. After the festivities came to a close, the couple was sent off to start their honeymoon in Bar Harbor, Maine.


Story by -Liesel Schmidt