Tommy & Jess met at the most romantic restaurant of all… a luxury five-star establishment known worldwide as Buffalo Wild Wings. Jess was bartending that night, and Tommy had come in with friends. As a joke, one of Tommy’s friends left his phone number on the check-and, also as a joke, Jess and her coworker decided to text him. What started as a laugh quickly turned into something more. During their very first conversation, after discovering they had an uncanny amount in common-their moms share a birthday, and they both claim Iron Man as the best Avenger-Tommy jokingly “proposed” through text with a Ring Pop GIF. They spoke long into the early morning hours. From that moment on, they were hooked. What began as a playful exchange turned into an instant spark, and their love story has been growing ever since.

Tommy & Jess were celebrating at a family Halloween party when it came time to announce the winners of the annual costume contest. To no one’s surprise, they took home the title of Cutest Couples Costume, a category they also won last year as well, by the way. Two years running! But then Tommy’s sister, Julianna, grabbed the microphone and revealed a new category: “The Most Surprised.” The winner? Jess. And she truly was. So surprised, in fact, that she actually walked away from the Groom-to-Be multiple times before finally turning back to him and accepting his proposal. Tommy made it impossible to say no, and the custom-designed ring didn’t hurt either. He had always known Jess’s dream proposal included both of their families. He also knew her obsession with all things "spooky season," and that night, surrounded by the people they love most, he made it happen.