Tommy & Jess met at the most romantic restaurant of all, a luxury 5 star restaurant.. Buffalo Wild Wings. Jess was working as a server and Tommy went in to eat with his friends. His friend left Tommy’s phone number (as a joke) and Jess & her coworker texted him (also, as a joke). Tommy actually proposed through text using a ring pop gif during their first ever conversation, after learning they had so much in common, their moms shared a birthday, and they shared the same favorite avenger: Iron Man. They became instantly infatuated with each other and their love story blossomed from there.

Tommy & Jess were at a family Halloween Party. It came time to call winners for the annual costume contest. Tommy & Jess actually did end up winning “Cutest Couple” costume. Then Tommy’s sister, Julianna announced that there was another category for the night: “The Most Surprised,” and that the winner was Jess. She was, indeed, the most surprised, so surprised that she even walked away from the Groom to Be many times before actually accepting his proposal. He made it impossible to say no, and the custom designed ring also helped, too. Tommy always knew that when it came time to propose, Jess wanted something where both of their families would be there to share in the moment!