Jack and Holly met in high school in 2018, when Holly was a junior and Jack was a sophomore. Jack had been nervous about reaching out to her, but on homecoming night, September 22nd, he finally worked up the courage to send her a message. Over the next year, their friendship grew stronger. Then, exactly one year later—on September 22nd, 2019—Jack asked Holly to be his girlfriend. Shortly after, they attended the next homecoming dance together.

The year they started dating, Jack moved about an hour away. Despite the distance, they stayed closely connected and continued to support each other—especially through their involvement in sports, which became a meaningful part of their relationship together.

In 2020, Holly graduated from high school and moved to Duluth, Minnesota, to begin college. A year later, in 2021, Jack graduated and chose to attend the University of Minnesota Duluth as well. After two years of long-distance, they were finally in the same place again!

They love exploring new places together and spending time traveling to many different states and destinations, creating memories along the way.

Both Holly and Jack graduated from the University of Minnesota Duluth in December 2024, celebrating the achievement side by side after years of growing together.

In August 2025, Jack proposed to Holly at her favorite place. Completely surprised, Holly had no idea it was coming—and she says it was the easiest "yes" she’s ever given.

Holly is currently teaching 5th grade, and Jack is an accountant holding both his CPA and CFP. They are soaking up every moment of engaged life and loving this sweet season together.