There Once Was a Girl from Nantucket (S01E05)

Title: A Date with a Local Legend Plot: Brian arranges a date for Joe with a woman known for her romantic history with nearly every guy on the island. As Joe prepares for the evening, he grapples with the reputation of his date, unsure of what to expect. The night unfolds with unexpected twists, leading to comical yet enlightening moments that challenge Joe’s preconceived notions about love and relationships. Ultimately, he discovers there's more to her story than meets the eye.