By the time Demi Moore met Bruce Willis in 1987, she had already been married and divorced, and was engaged to someone else — fellow actor Emilio Estevez. In fact, the future couple first crossed paths while attending the premiere of Estevez’s star vehicle, “Stakeout,” per InStyle. At the time, Willis had a role in the ABC series “Moonlighting” but was not nearly as big as Moore, who just a couple years prior had already starred in “St. Elmo’s Fire” and “About Last Night… .” In a 1991 interview with Vanity Fair, Moore revealed, “When I told my grandmother I was going out with him, she said, ‘Oh, I’ve read all about him in the National Enquirer. He’s really wild.'” However, Willis’ rep at the time did not ring true for Moore, who added, “I never saw that.”
The same night of the “Stakeout” premiere, Willis wooed Moore with his impressive bartending skills. “Bruce was looking at me a lot as he went through his bar moves, he was so attentive as the evening progressed,” Moore revealed (via ET) in “Inside Out.” Noticing Willis’ flirtatious behavior throughout the night, then-fiancé Estevez had commented to Moore, “He’s all over you, like a cheap suit in the rain.”
By the end of the evening, Willis was serious about getting to know Moore. He walked her to her car, the two exchanged numbers, and the rest is history.
