Shawn and Kristen met in high school and reconnected 15 years later when he messaged her to go to a Bruins game. She hesitated at first but Cheryl convinced her to take the opportunity to go to a free playoff game even though it was Mother’s Day. They had so much fun (and the Bruins won!) that they continued the date at Sam Walker’s Tavern where they split steak tips. The fear on Kristen’s face was evident when the bartender asked how they would like them cooked and Shawn responded “medium well” as she simultaneously said “medium rare” - this was the moment Shawn converted to medium rare meat only, good thing or her family might not have accepted him. After that night, Shawn and Kristen were inseparable and continued going to many Boston sports events including the Red Sox game a few days later when he asked Kristen to be his girlfriend on the green line. And the rest is history.

In February of 2025, Shawn planned a "diabetaversary" party to celebrate Kristen managing Type 1 Diabetes for 20 years. Little did she know this was a cover for something else he had planned in front of her closest family and friends. Unfortunately, Shawn's daughter, Natalie, woke up with a 103 degree fever so they spent the morning at urgent care where they were told she had the flu. Knowing that Natalie was so excited to be part of the proposal, Shawn dropped her off with his mom for the day and continued to celebrate Kristen's accomplishments as if that was all that was ever planned for the day. In hindsight, he probably should have updated some people but thankfully Kristen just thought the champagne was for being such a good diabetic. A few weeks later, Shawn and Natalie had come up with a new plan. Shawn, Kristen and Natalie headed into Moxie's in Seaport for brunch, their favorite meal. Shawn asked their waitress to take a photo of the 3 of them (not weird at all..) and then got down on one knee! Natalie opened her new hot pink purse, took out the perfect ring, and presented it to Kristen asking if she will officially become her step-mom. Of course Kristen said yes! Lots of hugs & kisses and cheers followed and continued at the after party Shawn had planned at Main Street Grille with the best family and friends, and the after after party at their house. Not the original plan, but still the best start to the rest of their lives!