Locker buddies since 5th grade, Olivia and Colt grew up together in Mazomanie & Black Earth, Wisconsin. Officially since Junior year of high school, Olivia and Colt are high school sweethearts - from high school prom to buying their first home, they always knew they wanted to spend the rest of their lives together.

On a week-long vacation to Punta Cana, Dominican Republic, Colt knew he wanted to pop the question in a beautiful setting. Smuggling the ring through O'hare International Airport without Olivia knowing (hoping security wouldn't search his bag and unveil the ring forcing him to propose in the middle of the airport), on the first night in Punta Cana Colt hid the ring in his underwear throughout drinks & dinner, he brought Olivia to the edge of the pier after sunset and asked Olivia to spend the rest of their lives together. Olivia surprisingly accepted and they spent the rest of their week-long vacation celebrating.