When did Angelina Jolie lose her virginity?

Angelina Jolie's first appearance on screen was at the age of five, where both daughter and father Jon Voight was in Lookin To Get Out.

Then she started working as a model when she was a teenager. Angelina Jolie has been in several relationship in the past. 

She got her first boyfriend when she was 14 years old and her mother, Marcheline Bertrand, let him live in their house.

She lost her virginity from there. She told OK, “I had started having sex with my boyfriend and the sex and the emotions didn’t feel enough. I was no longer a little girl. In a moment of wanting to feel closer to my boyfriend I grabbed a knife and cut him. He cut me back. We had an exchange of something and we were covered in blood, my heart was racing".

They dated for two years.