Billy and Jenna met thanks to their mutual friend John, who invited Jenna and her friend Meghan along a Spring Break trip to Kansas City, for you guessed it, some White Sox baseball. After going to their first two games together watching the White Sox lose, not to mention surviving a terrifying car ride home, Billy asked Jenna to dinner a few days later. Never leaving one date without another one planned the two officially became boyfriend and girlfriend on May 21, 2015.

In the Summer of 2017, Billy and Jenna planned to go on a Jay Buckley Baseball tour of the East Coast. This amazing trip consisted of five major league ballparks, a minor league game and a stop in Cooperstown. The last stop of the trip was at Yankee Stadium and Billy had something up his sleeve. His original plan of proposing in Monument Park was ruined due to some busy New York City traffic, so he had to make a quick decision and opted to propose in front of the Lou Gehrig display in the ballpark Yankee Museum. The reason for this was that Jenna's dad was a massive Gehrig fan and this would have extra special meaning to her. While Jenna browsed the Gehrig exhibit, Billy asked an attendant to take a picture of the two to help capture the moment. To his surprise, he was immediately told no and that they weren't allowed to take photos for museum guests. Billy quickly found a manager and hoped he'd be able to help ensure this plan would not fall apart as well. After explaining the significance of the spot and what he had planned the manager explained to Billy he could help make this moment even more special if he was able to wait a little longer. After a few long, nerve-wracking minutes walking around the museum checking out various artifacts, they were approached by the manager who struck up a casual conversation by asking Jenna who her favorite player was. Worrying her response would be someone other than Gehrig, thankfully, Jenna did not disappoint and quickly named her father's baseball hero. The manager told the couple he had something he'd like to show them and led us to a small back corner of the museum. Then, after shuffling around in a random broom closet for a minute, he pulled out a game-used Lou Gehrig bat. With special gloves on the two began taking pictures when suddenly Billy was on one knee quoting Gehrig himself and asking Jenna to make him "the luckiest man on the face of the earth" by becoming his wife, to which she of course said...Thank you.