It was a rainy June day in 2023 at the Lauderdale Yacht Club. Due to the weather, Jess and her friends were unable to go boating, so they took shelter under the Pavilion and grabbed a cool refreshment. This is where Jess and Bob first met—Bob was a regular on Sunday afternoons at the Pavilion, enjoying an Arnold Palmer and an LYC Club sandwich. After their encounter, Bob started following Jess on Instagram, occasionally exchanging messages with her.

Fast forward six months, and Bob bumps into Jess once again at the Lauderdale Yacht Club for a friend’s birthday. After working up the courage, he finally asks the beautiful Jess for her number—and gets it.

Four days later, they go on their first date. After a few fun outings (see photos below) and bonding over funny videos, things start to get more serious. Realizing Jess is a keeper, and after some in-depth conversations, Bob decide to make it official on March 17, 2024.

On May 3, Bob's birthday, Jess gives him a custom painting of his grandfather, Bobba, as a gift. Bob is instantly overwhelmed with emotion. In that moment, he realizes that one day he is going to marry Jess—she truly understands and loves him, giving a gift that means more than she even knows. From that moment on, Bob knows he must get permission from her family to make it happen.

After the Panthers win the Stanley Cup in Game 7, Bob and Jess fly to California to visit her family. Bob is working up the courage to have a conversation with her parents. After a great BBQ and time spent with her family, Jess’s dad, Johnny, makes a comment to Bob, saying, “Bob, your future mother-in-law needs another Fireball shot.” In that moment, Bob knows the conversation will be a little easier because they are on the same page. A couple of days later, Bob got permission.

Bob wants everything to be just right for the proposal! With family trips and parties stacking up, he waits for the perfect moment, making sure his brother Daniel gets his wedding shine first!

To pull off the perfect surprise, Bob collaborates with the GM of the Lauderdale Yacht Club to create a fake photo shoot called the "Member Spotlight," in which he and Jess would be featured. See the photo of the email Bob wrote, which the GM then sent from his work account. The stage was set.

Come November 4, 2024, it's game time. Bob ensures that all the family is in town and hidden before he and Jess head to the photo shoot. They arrive at one of their favorite spots at the yacht club, where the photographer sets Jess up for a picture. As she poses, Bob gets down on one knee and asks her to turn around to answer one very important question.

Jess in a Dress said Yes!!