Kelsey and Sam’s story began way back in 2004 at a Girl Scout dance held by the Prospect Heights Park District. Though they were in different grades (3rd and 5th), they stayed connected over the next few years through emails and landline calls—because, let’s face it, crossing paths in school was a rare event! Their friendship grew, and so did Sam’s crush on Kelsey. By 2006, he made his first move, buying her a Christmas present and personally delivering it to her door. Bold, right? Not long after, Sam summoned all his courage and asked Kelsey to be his girlfriend. Kelsey’s answer? A thoughtful, “Maybe when we’re older.” According to Kelsey, her mom had a little something to say about their two-year age gap —but for a few days, Sam proudly told anyone who’d listen that Kelsey Martin was as good as his… someday. Well, someday came around 13 years later. By then, they were 25 and 23. Sam had recently moved back to Chicago and decided to slide into Kelsey’s DMs in October 2019, asking her out. To his delight, she agreed. Over a dinner of soup dumplings, sparks flew, and a week later they were out together again. It wasn’t long before things really started to take off. While the pandemic was a tough time for many, for Kelsey and Sam, it became an opportunity to grow closer, spending lots of time together and with each other’s families. This time together deepened their bond, and it wasn’t long before they realized they wanted to spend forever with one another. On a rainy December night at Wrigley, Sam got down on one knee and asked Kelsey to marry him. They celebrated the engagement with family and friends, ready to start their journey toward the altar and beyond.