Kelsey and Brandon like to joke that they’ve been “off and on (mostly off)” for almost seven years — and that’s because their story goes all the way back to 2019. It all began at the last Schindler sibling graduation party (thanks, Maggie!). To celebrate, the rest of the crew decided to throw a good old-fashioned house party on Temple Street and invite everyone they knew. Among the guests was Brandon, who had just returned home from the Navy and went to school with Kelsey’s brother, Bobby. While Maggie and her friends were responsibly in bed, Kelsey and Brandon met for the first time — and quickly became the night’s “closers.” They hit it off instantly, but life had other plans. Over the next few years, they popped in and out of each other’s social media messages, keeping the spark alive from a distance. Finally, they went on their first official date — and it went great! Unfortunately, a pesky case of poison ivy for Brandon and a pesky case of Kelsey’s summer spent up in New Hampshire got in the way of date number two. Fast forward a year to the Patriots’ home opener. Maybe it was the emotion of Tom Brady’s tribute, but Brandon decided to reach out again and ask Kelsey the all-important question: “Why aren’t we dating?” They’ve been together ever since. Since then, they’ve been (very slowly) dating their way through the alphabet — and when it came time for the letter “H,” Brandon told Kelsey he’d gotten them a hotel in Boston. While walking to dinner along the waterfront, he surprised her with the biggest “H” of all — he asked her to marry him! Kelsey didn’t hesitate for a second, giving the night a double “H” when she said, “Hell yeah!”