The couple first crossed paths in eleventh grade English class, where they began a friendship with staring contests across the room. Their friendship took a hiatus when Jed moved to North Dakota and Caroline left for college, but they reconnected around February of 2017 when Jed moved back. It took a few weeks of convincing before Caroline agreed to go out with him, and neither have looked back since.

On their two year anniversary, Jed and Caroline went to Old Books on Front Street in Wilmington, an adorable bookstore that had sentimental value to Caroline. With live piano playing in the background and fairy lights above, Jed surprised Caroline with a ring and a beloved book she had been eyeing for a while. It was one of the most magical moments and marked the beginning of an entirely new journey for the two.