Rob Lowe, Emilio Estevez, Demi Moore and Melissa Gilbert

Photo: Getty Images

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At this 1985 pro-peace demonstration, Rob socialized with other Brat Pack members Emilio Estevez and Demi Moore, as well as former girlfriend Melissa Gilbert.

Though he shared a roller coaster relationship with Melissa, when Oprah asks Rob if he ever had a crush on his About Last Night co-star Demi, he responds, "Who didn't?"