Brad Pitt and Angelina Jolie’s oldest biological daughter has gone through an interesting journey that is worth telling. The actress already had adopted son Maddox, 21, and daughter Sahara, 18.

Both of them were orphans from their own countries. She started dating Brad Pitt and the couple gave birth to daughter Shiloh, who is currently 16. Together, Pitt and Jolie adopted son Pax, 19.

And eventually they had twins Knox and Vivienne, who are 14. They no longer date and all the kids spend most of their time with their mother, which has made daughter Shiloh go through a major transformation as she grows to become a young woman.

When she was younger, Shiloh liked using boys clothes and wanted her family to call her John.

She even started a process to make the transition to become a man but there was a sudden change when she turned 15. During the ‘Eternals’ premiere, we got to see Shiloh wearing a dress and even makeup.

This kept going until she started asking permission to go on dates with boys. But Angelina Jolie has a set of very strict rules in order to allow her to start dating.

She is only 16 years young, after all. Some parents might think this is a little too strict but those are Angelina Jolie’s rules.

In recent months, Jolie was spotted with actor Paul Mescal at a restaurant and rumors started circulating. The tabloids believed Jolie was actually dating a young man who is significantly younger then she is.

But as it turs out, Vanity Fair reported the one who was interested in dating the young actor is Shiloh. During a Life & Style interview, Jolie herself confirmed she must accompany her daughter and her potential suitor at all times during this age.

This might seem like an over-protecive mother but we are talking about a minor in this case. As far as Brad Pitt is concerned, there is no evidence he is heavily involved in this new stage of his daughter’s life.

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