Bailey Ruth Shimmin grew up outside of Monmouth at Lake Warren. She went to United High School and eventually attended Monmouth College.

Conner David Hill grew up outside of Biggsville. He attended West Central High School and started at Monmouth College.

In the Fall of 2019, Bailey and Conner began Monmouth College, where both were history majors and classics minors. In the Spring of their Freshman year, the two finally met in Elementary Latin held in the historic Wallace Hall.

It wouldn't be until months later that Conner would, very brilliantly, send Bailey a message on Instagram pretending not to know she was in his Latin class and begin a conversation.

However, Conner would leave Monmouth to attend Western Illinois University in the Fall of 2020. Thankfully, he continued to work at the Monmouth College Bookstore, which was located in the same building that Bailey lived in at the time.

The two had their first date on August 21st, where they went to the Wordsmith Bookshop in Galesburg, IL. Then after spending the day together ended the date with a romantic dinner of Arby's at the park.

Well she was my very mean boss at a publishing firm until her visa expired because she was from Canada. So in order for her to keep her job, we had to fake a relationship and engagement as we met my family in Alaska for my Grandma Betty's 80th Birthday. However, throughout our fake relationship, we found real love for each other.

Okay well it didn't happen exactly like that. Conner had planned the proposal for a long time in about February of 2023. He asked her parents for their blessing at a magical place called the Maple City restaurant. Then for the next few months, he worked with one of Bailey's sisters, Jennifer, (future maid of honor) to help plan the proposal. It took awhile to find the perfect engagement ring because Bailey had a specific cut style in mind, but eventually he found the perfect one to pop the question.

Once the ring came in, it was time to figure out the strategy behind the proposal. Bailey REALLY wanted her nails done before he proposed, so Conner through Jennifer asked Bailey's friend, Alison, (future bridesmaid), to take Bailey to get her nails done the Wednesday before the proposal. Conner also decided that he should propose on a Sunday because that was the day of the week that they spend the most time together. However, he planned a "Galesburg trip" for after church, so that Bailey knew to dress up a bit.

Conner knew he wanted to propose outside of Wallace Hall because that was where the two met; however in order to get Bailey there, he had her mom text her right after church to get yellow time sheets from a paper holder thing on the second floor of Wallace. These directions took Bailey's mind off of what could be happening, which set up the perfect proposal.

As the two were walking up the sidewalk to Wallace, Conner gave her a present which was her supposed late anniversary present. Bailey opened it right at the front of Wallace to find her favorite Harry Potter book, Half-Blood Prince. She opened up the book to see a bookmark Conner made that had their names on it as well as the word "Always." The bookmark was also on the chapter titled "The Unbreakable Vow." Conner then knelt down and asked her the question that would change their lives forever, "Which finger does the ring go on?"