It all started with a single Instagram post, a comment, and a direct message. Both of us followed Catholic influencer Emily Wilson, who shares quarterly "matchmaking" posts inviting thousands of Catholics to comment with short bios and what they seek in a partner. In May 2024, we both took a leap of faith. Kyle, in Charlotte, left a comment. Kate, in Chicago, read it and thought, “This is exactly what I’m looking for.” She slid into his messages and kicked off the conversation. Kyle later admitted his mindset was: “I’d get roasted if any of my buddies saw my comment. I can always delete it.” Spoiler: he got roasted anyway but the comment was a huge success—and a life-changing one. After several intentional FaceTime calls, we decided it was time to meet in person. Kate had a pre-planned girls’ trip to Charleston, SC, and suggested meeting there. Kyle drove three hours, and their first date became a six-hour whirlwind of deep conversation and laughter despite the 100-degree heat. We explored the city, bar-hopped with oysters and old fashioneds, and joked that we’d crammed 12 dates into one. From that moment, we committed fully, spending the next year and a half flying back and forth nearly every two weeks. Amid countless routine airport baggage-claim reunions, we adventured together across 13 states and five countries. In November 2025, Kyle made the big move to Chicago, switching law firms and braving the coldest Chicago winter in over a decade.
Kate’s family has a unique “tradition” of planning surprise trips for each other, orchestrated by a fictional character named “Charlie.” Kate played the role of “Charlie” during Kyle’s July 2024 visit to Chicago, blowing him away with a weekend of surprises. Bringing it full circle, Kyle planned a “Charlie”-style surprise trip to San Diego in January 2026 and proposed on a sailboat at sunset. We can confidently say we wouldn’t be here without the incredible support of our friends and family, who encouraged our leap of faith from the very beginning. Thank you for believing in us—we are truly blessed. K&K