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Feb 29, - People don't only regret giving in to their sexual urges — sometimes they also regret denying them. Brooke Shields, who waited until she was 22, told Health that she wished she had lost her virginity sooner, because she felt that if she had, "I would have been much more in touch with myself.". Mar 5, - Dear Heather,. Help! I am 15 years old and in January I lost my virginity. It was with a boy who I had known for two years and had very strong.