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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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 ↗
Serena Williams United States professional tennis player, 1995–2022
Any lost match is, of course, disappointing, but every loss is a lesson to be learned.
Recorded The Guardian, The Q&A, The Guardian, 30 January 2021 source ↗
David Schwimmer American actor
The lack of role models in leadership in the US, in particular our government.
Recorded The Guardian, The Q&A, The Guardian, 8 September 2007 source ↗
Una Stubbs British actress, television personality, and dancer
Never learning another language.
Recorded The Guardian, The Q&A, The Guardian, 23 April 2016 source ↗

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