It all started on July 3rd, 2021. Bailey was visiting home in Vermont for the 4th of July when she and her friends ended up at “Will Sudbay’s older brother’s place,” a lakefront apartment with a perfect view of the Burlington fireworks. Not knowing who this “older brother” was, Bailey started picking up beer cans to be helpful. A handsome guy walked over and said, “Don’t worry, you don’t have to clean.” She laughed, “I’m just trying to help — I don’t even know whose apartment this is,” and he smiled, shook her hand, and said, “This is my place. Hi, I’m Charlie.” The next day, Bailey couldn’t stop giggling with her friends about the cute guy from the apartment. She found him on social media, and Charlie sent a message thanking her for helping clean and asking if he could take her out for a drink. With Bailey living in New York City, it took over two months — and a little nudge from their mutual friend Mike — before that first drink date finally happened. From then on, they kept finding excuses to see each other despite the distance.

From the start, it was clear there was something special. Two early moments stand out: On their second date, Charlie caught three of Bailey’s friends — Rebeca, Grace, and Calie — spying from the brewery next door. He suggested they all join for an after-dinner beer. In that moment, Bailey knew that someone who welcomed her friends so easily was someone special. During Charlie’s first visit to NYC, Bailey took him to a Rangers game and, in an effort to impress him, placed sports bets — only for Charlie to point out she’d bet against herself and would lose either way. On the way home, she mispronounced “ominous” as “omNIous,” and then, while assuring Charlie the East Village was “actually pretty clean,” a rat ran up her leg, leaving them both in hysterics. That’s when Charlie realized how naturally he was drawn to Bailey’s silly, carefree personality. For two years, they filled the distance with spontaneous adventures, late-night calls, and cozy weekends together. In summer 2023, Bailey moved back to Vermont and, within a few months, moved in with Charlie. In September 2024, they left the lakefront apartment where they first met and moved into the townhouse they now call home. In April 2025, they brought home their golden retriever, Bodie, who quickly became their best little sidekick in life.

On Labor Day — September 1st, 2025 — Charlie surprised Bailey with an afternoon hike up Mount Philo in his hometown of Charlotte, where he proposed at the summit overlooking Lake Champlain. To make the day even more special, he arranged a surprise family dinner to celebrate afterward. Now they’re WFH office mates, co-dog parents, travel partners, late-night gigglers, and best friends — soon to be husband and wife. From that first night on the waterfront to now, they’ve kept bringing out the best in each other — and they can’t wait to see what’s ahead.