Pat and Katie met on a dating website named Coffee Meets Bagel. Pat asked Katie to go out to dinner at the Columbian Steakhouse called Las Tablas and she was impressed by his choice. While out to dinner, Pat's phone started blowing up because the Bears had picked Mitchell Trubisky 2nd overall in the 2017 NFL Draft. Even though he was freaking out, he managed to put his phone down and focus on the date. It went so well that they ended up going to a bar called Flagship for a night cap. Pat kissed Katie before they got in their Ubers to head home.

Pat took the pups, Goose & Graham, to get their nails trimmed. When he came back, he called Katie out to the back deck to check out Graham. Pat was holding Graham on his lap and asked Katie to check out his neck area. When Katie went to look, there was a ring attached to his collar. Pat asked Katie to marry him, and she said YES! Pat then said, go get ready, I have your favorite wine and we are going out to eat at your favorite restaurant! They had a wonderful evening celebrating and calling friends and family to let them know!