Rob Lowe and Melissa Gilbert

The '80s were a time of peak popularity for Rob Lowe and Melissa Gilbert, and Lowe makes another appearance on this list. This time, the Brat Pack teen idol was romantically involved with Melissa Gilbert, best known for her role in "Little House on the Prairie." Gilbert was just 17 years old when she embarked on a relationship with Lowe, and she later revealed in her memoir that she fell "instantly, hopelessly, and stupidly in love."

Their love story reached a significant milestone when Rob Lowe proposed to Melissa Gilbert in 1986. However, tragedy struck when they experienced a heartbreaking miscarriage, which ultimately led to the end of their relationship. Astonishingly, the actress tied the knot with actor Bo Brinkman only seven weeks after their breakup, marking a swift transition in her personal life.

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