Alissa and Caleb’s story began with an Instagram DM. On December 28, 2014, Caleb messaged Alissa on Instagram just to see what would happen. That one message turned into constant conversation, inside jokes, and the start of everything. In September 2015, Caleb asked Alissa to be his homecoming date and he has been her forever date ever since. Just a few weeks later, on October 15, 2015, they officially started dating during Caleb’s freshman year and Alissa’s sophomore year at Holy Cross. Alissa’s first impression of Caleb was that he was super cute and genuinely sweet. Caleb’s first impression of Alissa was that she was stunning. Somewhere between high school hallways, late nights, and growing up together, they became best friends. Over the years, Alissa and Caleb have navigated many seasons of life side by side from high school changes and college years to graduations, teaching, career growth, and landing in jobs they truly love. Through it all, they have continued choosing each other every single day. They moved into their first apartment at just 20 years old, learning early on what it meant to build a life side by side. Their family grew with the addition of three cats Syrus, Salem, and Sage who quickly became their whole world and made their house feel like home. On October 28, 2022, Caleb proposed and it felt like the easiest yes after everything they had already shared. After more than a decade together, they are still best friends, still growing, and still choosing one another every day. Now, on May 29, 2026, Alissa and Caleb cannot wait to celebrate their love, their journey, and the life they have built together surrounded by the people who mean the most to them.