One fateful day in late May of 2021, Anna and Riley came across each other's profiles on the dating app, Hinge. Anna had recently graduated from Indiana University in Bloomington and a few weeks into her new job with The Hershey Company, and Riley was roughly 1 year into building his law practice in Indianapolis and living with his brothers in Zionsville, IN. What started out as corny flirtations quickly blossomed into a budding romance. The two realized that they surprisingly had a lot in common. Both were homeschooled, raised in Indiana with similar backgrounds, graduated from and have an affinity for Indiana University, and possess a shared love for God and Jesus.
Riley and Anna decided to meet for the first time at Kilroy's Bar & Grill in Broad Ripple, IN on June 2, 2021, the day after Riley's 29th birthday. The two hit it off and decided to meet again. Their 2nd date was at Cancun Mexican Restaurant in Carmel, IN. Riley was excited to introduce Anna to their amazing margaritas. Anna agreed to meet Riley yet again, along with his best friend, and 2 brothers at The Rathskeller Biergarten on June 11, 2021 for an outdoor Clayton Anderson concert. Clayton Anderson is an Indiana-based Kenny Chesney soundalike country singer who frequents Bloomington concert venues and any Parr playlist. Please do not request or ask anyone to request "Slow Southern Night" at the wedding - but if you do, you will be popular.
Riley worked with Anna's younger sister, Emma, to stage a clever proposal at the IU campus in Bloomington - a location that holds a special place in Anna and Riley's relationship. Riley told Anna that the two would go on a Saturday outing to IU and later to have dinner with a family friend, but first would stop and visit with Emma, who was an incoming college sophomore and a New Student Orientation Leader at the time living on campus during the summer of 2022. Emma asked Riley and Anna if she could take them on a fake tour of the IU campus to practice for incoming students. The two embarked on a walkthrough of campus as Emma jokingly shared common IU traditions, jokes, and myths. The group ended up near the Sample Gates at a statue of Herman B. Wells (former IU president) sitting on a bench, where Emma asked Anna to "shake" Herman's hand for good luck - a common tradition for new students. As Anna turned her back to Riley to shake the statue's hand, Riley got on one knee.