In October of 2019, during game 4 of the World Series, Joanna spotted Tyler in a packed crowd at The Bullpen. She pointed him out to her friend Matt and said, "Oh he's cute... and tall." Being a good wingman, Matt dragged Joanna over to Tyler and said "My friend thinks she knows you from middle school." Tyler (thankfully) caught onto the pickup line and they spent the rest of the night together. A week later, Tyler asked Joanna on their very first date... and the Nationals went on to win the World Series.

On a fall Saturday, Tyler told Joanna they were having brunch with his friends in downtown Annapolis, but wanted to walk around the William Paca House & Garden beforehand. It was there he got down on one knee and proposed. Tyler planned ahead and had his friend photograph the whole proposal. Afterwards, Tyler surprised Joanna by taking her to brunch where her best friends were waiting to celebrate with them.