‘We weren’t supposed to do that’

Sandra Bullock and Jennifer Aniston’s friendship may seem natural now, but it almost never happened. In a revealing interview for Vanity Fair’s September issue, Bullock reflected on the challenges women faced in Hollywood when it came to forming bonds, especially between two big stars like them.

“We were from that time in the business where no one wanted the ladies to be friends — it was about pitting everyone against each other,” Bullock said. “We were told we weren’t supposed to do that — meaning like and respect and honor each other.”

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Despite these pressures, the two actresses first connected about 15 years ago at a mutual friend’s wedding. “We were just like, ‘Oh my God, we need to meet and cut loose,’” Bullock recalled. “And we did.” Aniston humorously noted that the drink she sent Bullock at the party was “definitely stronger than what she was sending me,” after Bullock woke up with a hangover the next day.

Over time, their friendship grew beyond Hollywood events. They found common ground in shared interests such as interior design, practical jokes, lavish trips, and even numerology readings.

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Bullock explained. “Nothing is for her alone ever. Everything she does is for everyone else included.” Their connection also runs deeper, shaped by some frightening real-life experiences. Both stars have faced stalkers, Bullock was home during a harrowing break-in in 2014, while Aniston recently dealt with a man crashing his car into her estate gate. 

Reflecting on the emotional toll, Bullock said, “It makes me think, ‘Do I really have to go outside and navigate the world?’ … It’s ongoing. It’s not a one-off. And it does create a mindset where your home also unfortunately becomes your fortress.”

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Their bond has helped each other through such struggles. Bullock described a moment on a flight when Aniston comforted her, saying, “She just held onto my hand and goes, ‘This is just a bump.’ I was like, ‘Who the f— are you right now?!’” Aniston also keeps Bullock motivated: “There’s a motivation of going, ‘Okay, we need to go somewhere. Where are we going?’ I’m desperately trying not to Howard Hughes myself.”

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The two stars share a quirky Hollywood link beyond friendship, they both once dated actor Tate Donovan at different times in the 1990s. Bullock dated Donovan from 1990 to 1995, before he went on to date Aniston from 1995 to 1998, even guest-starring on ‘Friends’ as Aniston’s character’s love interest. 

“I think her superpower is that she could very easily be hard, but she’s incredibly open,” Bullock said. “People want to know about her and understand where she is in life and want her to be happy.”