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As the whole O'Brien family reunites in Chesapeake Shores for the first time in years, Abby attempts to learn from her own father's mistakes to avoid missing out on her young daughters' lives. As she contemplates leaving Wall Street behind, her high school sweetheart Trace struggles to open up about the reason he left Nashville. Harboring resentment for both of her parents, Jess sets out to prove she doesn't need their help to open her bed and breakfast. But just as it seems this family can't find common ground, an unexpected confrontation proves the O'Briens can come together in a crisis.