In November 2014, two unsuspecting OkCupid users received notifications that someone had liked their profile. After a week of exchanging messages on the platform, Jack and Kate met for drinks at Penn Social in Washington, DC. A series of dates, from dinner at Bar Charley's to a Caps game at the Verizon Center, late-night drinks at POV to long walks on the National Mall, cemented that initial "like" online. A little less than three years after they met, Jack proposed!

Nestled in the hills of the Shenandoah Valley, Kate's family's house has always been a site of gathering for the entire extended family. On Labor Day 2017, Jack proposed during a walk around the local lake. Barely over the surprise of the engagement, and certainly not over the excitement, Kate was thrilled to find Jack's parents and sister waiting alongside her entire family back at the house. True to tradition, the long weekend at Bryce was filled with the two families celebrating over shared great meals, conversations, and activities.