In 2018, both Jack and Lindsay decided to give online dating a chance. They matched that February while at college, and Jack started the conversation by saying he was studying for a chemistry test. Lindsay replied by admitting she was procrastinating on her homework. A couple days later, after chatting back and forth, Jack and Lindsay decided to meet in person at a Starbucks on campus. They talked for a couple hours, about everything from college woes to their personal lives, and by the end of the conversation, they both felt a genuine connection!

The week before spring break of 2018, Jack and Lindsay were doing homework together in Lindsay’s dorm. They were talking about their time together and if they should make things official. They took a moment to consider, then both looked at one another and said they couldn't see themselves with anyone else. Jack then asked Lindsay to make their relationship official that night on March 6th, 2018!

After a year of dating and getting to know each other better, Jack and Lindsay decided they should celebrate their first anniversary being together by taking a their first trip together as a couple. They took a day's drive south to Culpeper, VA. where they explored the Shenandoah Mountains, the Luray Caverns, and as many wineries as they could before they needed to go back home. On the last day of the trip, Lindsay told Jack that there couldn't be a better opportunity to go visit her sister at JMU. The next morning, they woke up bright and early and made the trip to Harrisonburg to surprise Brooke and spend the day at JMU.

In early 2020, the first COVID lockdowns and travel agency crashes hit the U.S. economy. This presented Lindsay and Jack with a once in a lifetime chance to go to Hawaii at nearly half the price it would normally be. They bought tickets, started to book hotels, and then it all came crashing down when the lockdowns were tightened as COVID continued to spread. Disappointed, but not deterred, Lindsay and Jack decided to use the money they set aside to go to Hawaii to get their first apartment together in Fairfax, VA! They found a great listing that was in the heart of the city and barely twenty minutes away from just about anything, perfect for them to make the most of their first place together!

In August of 2020, Lindsay got a picture from her mother of a beautiful and healthy Boston Terrier. Curious, Lindsay asked her who's dog he was, to which her mom replied with "He's yours!". They took the following weekend to visit Lindsay's parents in Pennsylvania and meet the dog. Upon arrival, they instantly fell in love with the little guy, named him Bosco, and took him back to Virginia with them. Since then, Bosco has been a crazy and lovable addition to the family, taking part in every adventure and keeping his dad company while he worked from home.

Lindsay's dad, Jason, had recently purchased a home in Toledo, OH., and invited Jack, Lindsay, Brooke, and Michaela up to surprise Lindsay's grandmother for her birthday and to see the house. They took a flight up to Detroit, MI., where Jason met them at the airport and drove them to his home. The following day, Jason invited his parents over to his house and everyone threw grandma Barb a surprise party! That evening, as the party carried on, everyone but Jack and Jason left to go get some groceries for the evening. Jack used this opportunity to announce his intent to marry Lindsay to her dad, and asked for her hand. Jason was delighted, gave his blessing, and couldn't wait to see what the future held for them!

Six months prior, in June of that year, Jack had purchased and received Lindsay's engagement ring and was eagerly awaiting an opportunity to use it to propose. Weeks and months went by as Jack and Lindsay lived out their daily lives, not doing anything particularly special that would warrant a proposal. However, around Christmas time, Lindsay's dad was planning on being in town to visit his daughters. Lindsay's sister told Jack that now would be the perfect time to propose, so Jack stayed vigilant and waited for the right moment to propose. On Christmas eve, Lindsay's dad got into town early and the group (Lindsay, Jack, Brooke, and Michaela) all decided to meet him at a local brewery in Manassas, where they were given a personal igloo outside to dine in. There, they enjoyed a few craft brews and a pizza before things settled down. At this point, Brooke and Michaela had their cameras out and kept making faces at Lindsay and Jack. Eventually, Jack took the hint, got down on one knee, and asked Lindsay to marry him!