Caleb always admired Bailey from afar during their undergraduate years at Vanderbilt. Their junior year, Bailey invited Caleb to a sorority date function. Despite his best efforts, Caleb fell in love with Bailey by the time the evening was over. They kept in touch throughout the summer, while Caleb remained in Nashville and Bailey studied abroad in Italy. When they returned for their senior year, Caleb asked Bailey out on their first date. She said no - she just wanted to be friends. But that wasn't the end of their story.

Three full years later, Caleb had moved to Houston, and Bailey was in her final year of graduate school in Nashville. They reconnected at a New Years Eve Party, where they spent most of the night talking to each other and catching up. But the night ended, and Caleb went back to Texas. A few months later, Bailey found out she was assigned to an away rotation in Caleb's hometown of Jackson, Tennessee. How Providential! She called him, asking for suggestions for housing. Caleb jumped on this opportunity to assist and talk to Bailey. He found housing for her and called her every Thursday afternoon on her drive back to Nashville. She would always answer. After a few weeks of staying in touch, Caleb asked Bailey out on another date. This time - she said yes. Caleb flew into Nashville a few weeks later, and they went on their first date. One dinner turned into a full weekend of activities and dates, with Caleb asking Bailey to come visit Houston as he left Nashville. She did.

On August 22, 2019, Caleb flew to Memphis to ask Bailey to marry him. Prior to the proposal, Bailey knew an engagement was coming. However, she had no idea when, where, or how it would happen. She was actually beginning to wonder whether she misunderstood their timeline, as her close friends and family were suggesting that an engagement may come later than she expected. The weekend before the proposal, Bailey had a friend stay with her in Memphis. Following her departure, she told Bailey she wanted to send her a bottle of wine from a family favorite vineyard as a thank you for letting her stay. Bailey was instructed to be at home on Thursday, August 22nd, from 5-6 pm to sign for the delivery. Thursday came and Bailey divinely had an easy day seeing patients at clinic. She was home by 5 o'clock and was ready, waiting for the delivery. A knock at the door came, but when Bailey opened it there was no delivery man, service van, or bottle of wine in sight. That is when it hit her. It was Caleb. She ran from the front to the side door and saw Caleb standing there with flowers and a bottle of champagne. It was happening. Overjoyed with excitement, Bailey starting crying while Caleb tried to "keep it together". They then made their way to the Memphis Botanical Gardens, where Caleb proposed under the shelter of a beautiful outdoor chapel.

Bailey and Caleb were long-distance for their entire season of dating. Long-distance dating was challenging, but Bailey and Caleb were committed to investing in and loving each other despite being in separate cities. They traveled back and forth from Houston and Memphis, as well as to Nashville, Tampa, Orlando, Chicago, Jackson, Las Cruces, and Nicaragua. Late night Face-Times and early morning phone calls kept them going during their weeks apart, and their moments together were precious. They are beyond grateful for each other and for the Lord's abundant blessing in their relationship. They constantly want to strive to show the love the Lord has shown them to each other and those around them.