Olivia and Kyle first met when they were in the same CCD class at St. Mary's Church in Shrewsbury. As a class, they went on a mission trip to Newark, NJ, and that was the first time they spent time together. Months later, at Shrewsbury High School's homecoming dance, Olivia decided in her best friend Robin's car that she had to go talk to Kyle. They danced the night away and have been boogying together ever since.

Kyle brought Olivia to one of their favorite Boston museums: Isabella Stewart Gardner museum. Isabella's courtyard was a perfect fit for a proposal, overflowing with purple flowers that was almost certainly a wink from Olivia's grandma. After saying yes, they walked through Boston to the North end to get martinis and pasta at their favorite Italian restaurant.