Jacob and Riane met their freshman year of high school at Brebeuf Jesuit Preparatory School. They were fast friends, connecting through shared classes and friend groups. Although they both felt an attraction, they focused on maintaining their friendship for the first few years of school. By spring semester of sophomore year, Jacob was done being in the "friend zone". He asked Riane on a date, and although she initially insisted that she didn't want to ruin the friendship, she didn't resist for long. After seeing how serious he was about his feelings, Riane decided to take the risk and let him take her on a date. On May 8, 2009, their relationship officially began. They graduated from high school together, and both moved to Bloomington to complete undergraduate and graduate-level programs at Indiana University. When their studies were finally completed, the couple moved to Chicago together to begin their adult lives.

After 10.5 years of dating, Jacob proposed to Riane on a joint family vacation to Hawaii. Although Riane had guessed correctly that the proposal would happen on the trip, Jacob still kept his plans under wraps. The first couple days of the trip passed without any sign of a proposal. Then, they went on a family sight-seeing and photography tour all around the Big Island, which Riane incorrectly thought was planned by her mother and not Jacob. After sunset came and went, she was convinced it wouldn't happen that day, but she was wrong. The tour ended on top of Mauna Kea, the darkest place in the world, where the stars are indescribably bright. While star gazing with both of their families watching, Jacob got down on one knee and asked Riane to marry him. He later revealed that he'd starting planning this proposal when his family had visited the same spot seven years earlier. Riane said yes!

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