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The question

What disappointment has stayed with you longest?

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The Guardian, to a different person each week, The Q&A

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Eve Ensler American playwright, performer, feminist, and activist
That most men have not yet come to understand the impact and the devastating consequences of violence against women.
Recorded The Guardian, The Q&A, The Guardian, 22 June 2019 source ↗
Nora Ephron Journalist, essayist, screenwriter and film director
The movies I made that didn't work.
Recorded The Guardian, The Q&A, The Guardian, 5 September 2009 source ↗
Barack Obama 44th President of the United States, 2009–2017; United States Senator from Illinois 2005–2008
If you ask me where has been the one area where I feel that I've been most frustrated and most stymied it is the fact that the United States of America is the one advanced nation on earth in which we do not have sufficient common-sense, gun-safety laws. Even in the face of repeated mass killings. … And for us not to be able to resolve that issue has been something that is distressing. But it is not something that I intend to stop working on in the remaining 18 months.
Recorded Jon Sopel, BBC News interview, the White House, 24 July 2015 source ↗

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