In September of 2017, Barry journeyed to Cuttyhunk Island to play music at the 21st Annual Fishing Tournament Party. Tamalin was living on the island gathering inspiration for her oil paintings, and running the Avalon Inn. She, her sister Heron, and her friend Hannah danced the night away at the party, and Tam caught Barry's eye. He introduced himself to her on set break. That fall, Barry made many trips across Buzzards Bay in his 14-foot boat to visit Tam, often in the middle of the night after his music gigs. They fell in love on the windswept island, and one year later got engaged overlooking the cliffs of Cuttyhunk's West End.