Even though she lived in TX, Tassia was fortuitously assigned Illinois, Jim's home state, as a sales territory in 2014. After a few friendly run-ins at happy hours and trainings in Chicago, Jim and Tassia took a trip to Boston for a charity golf tournament. A casual mention to a co-worker that she was "surprised Jim was still single" since he was "so cute and nice" led to a rooftop dinner in the NorthEnd and the rest was history.

After 9 months of long distance dating, 2.5 years of making a life together in Chitown, a home purchase, and a puppy, Jim was finally ready to pop the question. After a fun day spent together in Galena, IL, a town both had wanted to visit for years, Jim led Tassia on a post-dinner walk on a cold, starry, December night. Stopping in a lighted gazebo overlooking the little town, Jim got down on one knee and asked Tassia to marry him.