12. Brooke Shields – Dean Cain
Brooke Shields is a classic beauty. The model-turned-actress waited until she was 22-years-old to give away her virginity. The lucky man was none other than Superman himself, Dean Cain. Shields had a vow of chastity but that fell to the leading man. And unlike many on this list, their relationship to this day is strong and unwavering. They are friends who have a mutual love and respect for one another. Cain had this to say: “We are still great friends…I was in love with her, certainly, we were in college; sweethearts.” Cain encouraged Shields to come clean about their relationship in her biography.
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