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Angelina Jolie’s son, Maddox, has always lived a very private lifestyle, so there are surprising things most might not know about him. What audiences have learned about Maddox has usually come from his mother, who’s been candid about raising him on occasion. In one interview, Jolie even gave insight on what it was like to hear Maddox speak for the first time. But although the moment was a joyous occasion, she admitted that the memory couldn’t help but make her a bit sad.

Angelina Jolie was all alone when Maddox reached this milestone

Angelina Jolie posing in a white outfit at the 40th Annual Santa Barbara International Film Festival: Maltin Modern Master Award Honoring Angelina Jolie.
Angelina Jolie | JB Lacroix/FilmMagic

Having Maddox gave Jolie a lot of memories to cherish. She recalled very vividly stumbling onto her son when she was visiting an orphanage in Cambodia. She took Maddox in after forming an immediate bond with him after failing to do so with other kids at his orphanage.

“I didn’t feel a connection with any of them,” she once told Vanity Fair (via People).

“They then said, ‘There’s one more baby.’ That’s when she saw Maddox lying in a box suspended from the ceiling. “I cried and cried,” Jolie added.

Although Jolie was in a relationship with Billy Bob Thornton when she took home Maddox, the pair would eventually break up. Jolie would raise Maddox as a single mother for a while. This meant she had to enjoy some of her most memorable moments with her son alone.

“There were so many times with Mad when he was growing up that I’d be up in the middle of the night, exhausted, rocking him. Nobody was there—except for friends—who saw me exhausted, who appreciated my efforts,” Jolie once said according to Live Journal.

She admitted that she was also a bit disappointed she had no one to celebrate with when Maddox started speaking.

“Nobody was there whom I could look at or explode in excitement with when Mad said his first word,” she said. “That was a bit sad. It made me very close to Mad but there’s the joy now of waking up in the middle of the night, like last night, and looking at the other exhausted parent, sharing the burden and learning, smiling about a child’s new tooth and just enjoying children. As a woman, having a partner who appreciates you as a mom, who remembers your history with your children is special.”

“Even though I had Maddox, I didn’t have a family somehow,” she added.

Angelina Jolie recently cried when Maddox reached this other important milestone

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A lot has changed since Jolie first picked up Maddox from his Cambodian orphanage. She adopted and gave birth to a few other kids, which she and Pitt would raise together before their shocking divorce. Nowadays, Maddox and his siblings are all grown up, with some of them already college students. Maddox was first of many kids that Jolie had to send away to school. The Wanted star seemed to get even more emotional saying goodbye to Maddox than when she first heard him speak. This time, she couldn’t help but shed tears at watching him leave the nest.

“Oh my god, like, embarrass-your-children ugly cry,” she told ET. “I also just at some point had the big [sun]glasses. The amount of times I turned and waved… I do know it was the one moment in my life… I think I turned around six times before the airport just kind of [disappeared]. And he sweetly stayed and kept waving, knowing that I was gonna keep turning around. You could feel he knew he couldn’t leave.”

“It’s nice to know that he knows how much he’s loved. But yeah, I miss him. I miss him,” she added.