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The Time of Our Lives follows the lives of the extended Tivolli family as they navigate their way around relationships, raising kids, love, careers, divorce, disability and finding happiness. Elder brother Matt is a high-flying sports agent struggling with his obsessive wife Caroline. Younger brother Luce runs a much more relaxed household with long-time partner Bernadette, despite a chaotic schedule and financial pressures. Chai Li, the youngest, was adopted from Vietnam as a baby and is a successful and happy thirty-something until her world is shattered by a humiliating turn of events. Herb has known the family since childhood.