Jack technically met Katie a long time ago. He just knew her as the girl Grace would walk to school with. Each morning on the way to Northwest he'd drop Grace off on Wampanoag so she could walk to St. Tims with Katie. Grace reintroduced the two of them fifteen years later at a bar in West Hartford, and later that night Jack texted Kir saying "That Katie Captains gonna be my wife".

Jack decided early on he wanted pure surprise. That's why he picked a Thursday evening in January, right after all the holiday festivities wrapped up. He texted Katie that afternoon saying it had been a tough day at work, and he needed a drink and a night out for dinner. Always so supportive, and always in for spontaneous nights, Katie didn't think twice of it. She was in. She made them a reservation at Barcelona... Little did she know, Jack had a whole evening planned for them already. They walk to Barcelona, and on the way Jack stops by the local violinist busking on the corner, dropped him a few dollars and asked him to play "Wildest Dreams". Katie thought he was just being funny, but soon she was shocked to find Jack on one knee asking her to marry him. Pure shock. She didn't see it coming at all. In fact, she was so distracted she also had no idea everyone was waiting for them at Barcelona. They walk in, she innocently tells the hostess how they just got engaged, and that they planned to facetime her Mom once they got seated. The hostess then leads the way to their "table", where she opens the door to 30 of their closest family and friends waiting to surprise her once again. She had no idea. Just as planned.